Production Method 1

2055648-50-3

86953-79-9

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Ethyl acetate ;  10 min, rt

Reference

A novel use of Boc-Oxyma as reagent for tert-butoxycarbonylation of amines and amino acid esters

Robert, Alice R.; et al, Chemical Data Collections, 2020, 30,

Production Method 2

24424-99-5

86953-79-9

Reaction Conditions

1.1 Reagents: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  0 °C; 10 min, 0 °C; 0 °C → rt; 24 h, rt

Reference

Dual Benzophenone/Copper-Photocatalyzed Giese-Type Alkylation of C(sp3)-H Bonds

Abadie, Baptiste; et al, Chemistry - A European Journal, 2019, 25(70), 16120-16127

Production Method 3

24424-99-5

86953-79-9

Reaction Conditions

1.1 Catalysts: Amberlyst 15 Solvents: Ethanol ;  < 1 min, rt

Reference

An efficient and highly chemoselective N-Boc protection of amines, amino acids, and peptides under heterogeneous conditions

Jahani, Fatemeh; et al, Monatshefte fuer Chemie, 2011, 142(10), 1035-1043

Production Method 4

151259-38-0

86953-79-9

Reaction Conditions

1.1 Catalysts: Grubbs' catalyst Solvents: Dichloromethane ;  overnight, rt

Reference

Iron- and Cobalt-Catalyzed Arylation of Azetidines, Pyrrolidines, and Piperidines with Grignard Reagents

Barre, Baptiste; et al, Organic Letters, 2014, 16(23), 6160-6163

Production Method 5

86953-79-9

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Cuprous iodide ,  Gold trichloride ;  0.1 MPa, rt; 24 h, 0.4 MPa, rt

Reference

Sustainable Route Toward N-Boc Amines: AuCl3/CuI-Catalyzed N-tert-butyloxycarbonylation of Amines at Room Temperature

Cao, Yanwei ; et al, ChemSusChem, 2022, 15(4),

Production Method 6

5176-27-2

86953-79-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Triphenylphosphine ,  [(1,2,5,6-η)-1,5-Cyclooctadiene](2,4-pentanedionato-κO2,κO4)rhodium Solvents: Isopropanol

Reference

Hydrogenation of five-membered heteroaromatic compounds catalyzed by a rhodium-phosphine complex

Kuwano, Ryoichi; et al, Chemistry Letters, 2000, (4), 428-429

Production Method 7

1289386-88-4

86953-79-9

Reaction Conditions

1.1 Reagents: Cesium carbonate ,  Cesium formate Catalysts: 3,5-Bis(1,1-dimethylethyl)[1,1′-biphenyl]-4-ol ,  Cysteine Solvents: Dimethylformamide ;  4 h, rt

Reference

Phenolate anion-catalyzed direct activation of inert alkyl chlorides driven by visible light

Wei, Delian; et al, Organic Chemistry Frontiers, 2021, 8(22), 6364-6370

Production Method 8

170491-63-1

86953-79-9

Reaction Conditions

1.1 Reagents: 2,4,6-Trimethylpyridine Catalysts: Tetrabutylammonium chloride ,  Iron chloride (FeCl3) ,  Bis[2,4,6-tris(1-methylethyl)phenyl] disulfide Solvents: 1,2-Dichloroethane ;  48 h, rt

Reference

Iron-Catalyzed C-C Single-Bond Cleavage of Alcohols

Liu, Wei; et al, Organic Letters, 2021, 23(21), 8413-8418

Production Method 9

15761-39-4

86953-79-9

Reaction Conditions

1.1 Reagents: Phenanthrene ,  1-Dodecanethiol ,  1,4-Dicyanobenzene ,  Sodium hydroxide Solvents: Acetonitrile ,  Water ;  6 h

Reference

Decarboxylative reduction of free aliphatic carboxylic acids by photogenerated cation radical

Yoshimi, Yasuharu; et al, Chemical Communications (Cambridge, 2007, (48), 5244-5246

Production Method 10

24608-52-4

86953-79-9

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dichloromethane ;  0 °C; 16 h, rt

Reference

Copper catalyzed late-stage C(sp3)-H functionalization of nitrogen heterocycles

Chang, Zhe; et al, Nature Communications, 2021, 12(1),

Production Method 11

86953-79-9

Reaction Conditions

Reference

stereoselective cross-coupling of chiral amino acid chlorides and hydrocarbons through mechanistically controlled Ni/Ir photoredox catalysis

Lee, Geun Seok; et al, Nature Communications, 2022, 13(1),

Production Method 12

86953-79-9

Reaction Conditions

1.1 Reagents: Thiophenol Catalysts: Iridium(1+), [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]bis[3,5-diflu… Solvents: Methanol ,  Acetone ;  16 h, rt

Reference

Catalytic protodeboronation of pinacol boronic esters: formal anti-Markovnikov hydromethylation of alkenes

Clausen, Florian; et al, Chemical Science, 2019, 10(24), 6210-6214

Production Method 13

73286-70-1

86953-79-9

Reaction Conditions

1.1 Reagents: Water ,  Diboronic acid Catalysts: Palladium Solvents: Dichloromethane ;  60 h, rt

Reference

Tetrahydroxydiboron-Mediated Palladium-Catalyzed Transfer Hydrogenation and Deuteriation of Alkenes and Alkynes Using Water as the Stoichiometric H or D Atom Donor

Cummings, Steven P.; et al, Journal of the American Chemical Society, 2016, 138(19), 6107-6110

Production Method 14

73286-70-1

86953-79-9

Reaction Conditions

1.1 Reagents: Water ,  Pinacolborane Catalysts: Palladium diacetate Solvents: Dichloromethane ;  12 h, 25 °C

Reference

Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration

Wang, Yong; et al, Advanced Synthesis & Catalysis, 2020, 362(19), 4119-4129

Production Method 15

149682-81-5

86953-79-9

Reaction Conditions

1.1 Reagents: Phenyllithium Solvents: Diethyl ether ,  Butyl ether ;  rt → 0 °C; 30 min, 0 °C → rt
1.2 Reagents: Thiophenol Catalysts: Iridium(1+), [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]bis[3,5-diflu… Solvents: Methanol ,  Acetone ;  16 h, rt

Reference

Catalytic protodeboronation of pinacol boronic esters: formal anti-Markovnikov hydromethylation of alkenes

Clausen, Florian; et al, Chemical Science, 2019, 10(24), 6210-6214

Production Method 16

59433-50-0

86953-79-9

Reaction Conditions

1.1 Reagents: Sodium carbonate Catalysts: Bis(2-pyridylmethyl)amine ,  Ferric nitrate ,  Bis[2,4,6-tris(1-methylethyl)phenyl] disulfide Solvents: 1,2-Dichloroethane ,  Water ;  20 h

Reference

Chemoselective Decarboxylative Protonation Enabled by Cooperative Earth-Abundant Element Catalysis

Lu, Yen-Chu ; et al, Angewandte Chemie, 2023, 62(3),

Production Method 17

170491-63-1

86953-79-9

Reaction Conditions

1.1 Catalysts: Tetrabutylammonium chloride ,  9,10-Diphenylanthracene ,  Cerium trichloride ,  Bis[2,4,6-tris(1-methylethyl)phenyl] disulfide Solvents: Acetonitrile ;  24 h, rt

Reference

Dehydroxymethylation of Alcohols Enabled by Cerium Photocatalysis

Zhang, Kaining; et al, Journal of the American Chemical Society, 2019, 141(26), 10556-10564

Production Method 18

236101-14-7

86953-79-9

Reaction Conditions

1.1 Reagents: Lithium hydroxide Solvents: Tetrahydrofuran ,  Water
1.2 Reagents: Potassium tert-butoxide Solvents: Dimethylformamide

Reference

N-Boc and N-Cbz ethyl oxamates: new Gabriel reagents

Berree, Fabienne; et al, Synthetic Communications, 1999, 29(15), 2685-2693

Production Method 19

91837-45-5

86953-79-9

Reaction Conditions

1.1 Reagents: Tetrabutylammonium tetrafluoroborate ,  Dithiothreitol Solvents: 1,2-Dimethoxyethane ;  4 h, 20 °C

Reference

Catalyst-Free Decarboxylation of Carboxylic Acids and Deoxygenation of Alcohols by Electro-Induced Radical Formation

Chen, Xiaoping; et al, Chemistry - A European Journal, 2020, 26(15), 3226-3230

Production Method 20

117625-90-8

86953-79-9

Reaction Conditions

1.1 Catalysts: 1,3-Bis(diphenylphosphino)propane ,  Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]dirhodium Solvents: Xylene ;  18 h, 160 °C

Reference

Ligand enabled none-oxidative decarbonylation of aliphatic aldehydes

Li, Bo; et al, Chinese Chemical Letters, 2023, 34(7),

Production Method 21

59378-75-5

86953-79-9

Reaction Conditions

1.1 Reagents: 2,4,6-Trimethylpyridine ,  Ammonium persulfate Solvents: DMSO-d6 ;  16 h, 40 °C

Reference

Direct Hydrodecarboxylation of Aliphatic Carboxylic Acids: Metal- and Light-Free

McLean, Euan B.; et al, Organic Letters, 2022, 24(2), 686-691

tert-Butyl pyrrolidine-1-carboxylate Raw materials

• Di-tert-butyl dicarbonate
• tert-butyl 2,5-dihydropyrrole-1-carboxylate
• 1-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid
• Acetic acid, 2-[(4-bromobutyl)[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-, ethyl ester
• tert-butyl 3-chloropyrrolidine-1-carboxylate
• Boc-L-Pro-OH
• tert-butyl 2-formylpyrrolidine-1-carboxylate
• tert-Butyl diallylcarbamate
• Pyrrole-1-carboxylic Acid tert-Butyl Ester
• Acetic acid, 2-cyano-2-[[[(1,1-dimethylethoxy)carbonyl]oxy]imino]-, ethyl ester
• tert-Butyl chloroformate
• tert-butyl (2R)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolidine-1-carboxylate
• 1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid
• Tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate
• 1-(tert-butyl) 2-(1,3-dioxoisoindolin-2-yl) (S)-pyrrolidine-1,2-dicarboxylate

tert-Butyl pyrrolidine-1-carboxylate Preparation Products

• tert-Butyl pyrrolidine-1-carboxylate (86953-79-9)

• 1. An artificial CO-releasing metalloprotein built by histidine-selective metallation?
  Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?o Chem. Commun., 2015,51, 3993-3996
• 2. An approach to biodegradable star polymeric architectures using disulfide coupling?
  Jingquan Liu,Huiyun Liu,Zhongfan Jia,Volga Bulmus,Thomas P. Davis Chem. Commun., 2008, 6582-6584
• 3. An artificial blood vessel implanted three-dimensional microsystem for modeling transvascular migration of tumor cells?
  Xue-Ying Wang,Ying Pei,Min Xie,Zi-He Jin,Ya-Shi Xiao,Yang Wang,Li-Na Zhang,Yan Li,Wei-Hua Huang Lab Chip, 2015,15, 1178-1187
• 4. Aggregated-fluorescent detection of PFAS with a simple chip
  Cheng Fang,Jinjian Wu,Zahra Sobhani,Md. Al Amin,Youhong Tang Anal. Methods, 2019,11, 163-170
• 5. An apparatus for testing water by measurement of its electrical conductivity
  Analyst, 1912,37, 538-543

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolidines Pyrrolidine carboxylic acids and derivatives Pyrrolidine carboxylic acids
• Solvents and Organic Chemicals Organic Compounds Heterocyclic Compounds

Introduction to Tert-Butyl pyrrolidine-1-carboxylate (CAS No. 86953-79-9)

Tert-butyl pyrrolidine-1-carboxylate, with the chemical formula C?H??NO?, is a significant compound in the field of pharmaceutical and chemical research. This compound, identified by its CAS number 86953-79-9, has garnered attention due to its versatile applications in synthetic chemistry and medicinal chemistry. The structure of tert-butyl pyrrolidine-1-carboxylate features a pyrrolidine ring substituted with a tert-butyl group and a carboxylate moiety, making it a valuable intermediate in the synthesis of various bioactive molecules.

The tert-butyl pyrrolidine-1-carboxylate moiety is particularly interesting because of its stability and reactivity, which make it a preferred choice for modifying the pharmacokinetic properties of drug candidates. In recent years, there has been a growing interest in the development of novel therapeutic agents that leverage this scaffold for improved efficacy and reduced side effects. The tert-butyl group, in particular, contributes to the lipophilicity of the molecule, which can enhance membrane permeability and oral bioavailability.

One of the most compelling aspects of tert-butyl pyrrolidine-1-carboxylate is its role in the synthesis of protease inhibitors. Proteases are enzymes that play crucial roles in various biological processes, including inflammation, blood clotting, and viral replication. Inhibiting these enzymes has been a major strategy in drug development, particularly for conditions such as HIV/AIDS, cancer, and autoimmune diseases. The pyrrolidine ring in tert-butyl pyrrolidine-1-carboxylate provides a suitable platform for designing molecules that can selectively bind to and inhibit specific proteases.

Recent studies have highlighted the potential of tert-butyl pyrrolidine-1-carboxylate as a key intermediate in the development of next-generation antiviral drugs. For instance, researchers have utilized this compound to synthesize derivatives that exhibit potent activity against RNA viruses. The carboxylate group allows for further functionalization, enabling the creation of molecules with enhanced binding affinity and selectivity. This has been particularly relevant in the context of emerging viral threats, where rapid development of antiviral agents is critical.

In addition to its applications in drug discovery, tert-butyl pyrrolidine-1-carboxylate has found utility in materials science. The unique structural features of this compound make it suitable for use as a ligand in catalytic systems. For example, it has been employed in transition metal-catalyzed reactions where its steric hindrance and electronic properties contribute to high yields and selectivity. Such applications underscore the broad versatility of tert-butyl pyrrolidine-1-carboxylate across multiple scientific disciplines.

The synthesis of tert-butyl pyrrolidine-1-carboxylate typically involves multi-step organic reactions, often starting from readily available precursors such as tert-butanol and gamma-butyrolactone. Advanced synthetic methodologies have been developed to improve yield and purity, making this compound more accessible for research purposes. Techniques such as asymmetric synthesis have been explored to produce enantiomerically pure forms of tert-butyl pyrrolidine-1-carboxylate, which are essential for applications in pharmaceuticals where chirality plays a critical role.

From a regulatory perspective, tert-butyl pyrrolidine-1-carboxylate (CAS No. 86953-79-9) is not classified as a hazardous or controlled substance under current international guidelines. This classification simplifies its handling and distribution, making it an attractive choice for academic and industrial research laboratories alike. However, standard laboratory practices should always be followed to ensure safe handling and storage.

The future prospects for tert-butyl pyrrolidine-1-carboxylate are promising, with ongoing research exploring new synthetic routes and applications. As our understanding of biological systems continues to evolve, compounds like tert-butyl pyrrolidine-1-carboxylate will likely play an increasingly important role in addressing complex medical challenges. Whether used as an intermediate in drug development or as a component in advanced materials, this versatile molecule exemplifies the intersection of chemistry and innovation.

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