Production Method 1

13139-14-5

82689-19-8

Reaction Conditions

1.1 Reagents: 4-Methylmorpholine Solvents: Tetrahydrofuran ;  30 min, 0 °C
1.2 Reagents: Methyl chloroformate ;  1 h, 0 °C
1.3 Reagents: Sodium borohydride Solvents: Water ;  4 h, 0 °C

Reference

Synthesis and antimicrobial activities of amides of chiral benzyl ethers of N-Boc protected aminols of L-amino acids with succinic acid

Mumtaz, Salma; et al, Journal of the Chemical Society of Pakistan, 2015, 37(2), 407-417

Production Method 2

33900-28-6

82689-19-8

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  4 h, 0 °C
1.2 Reagents: Citric acid Solvents: Water ;  > 1 min

Reference

Development of N-Hydroxycinnamamide-Based Histone Deacetylase Inhibitors with an Indole-Containing Cap Group

Zhang, Yingjie; et al, ACS Medicinal Chemistry Letters, 2013, 4(2), 235-238

Production Method 3

24424-99-5

73-22-3

82689-19-8

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  4 h, 80 °C; 80 °C → 0 °C
1.2 Reagents: Sodium sulfate Solvents: Water
1.3 Solvents: 1,4-Dioxane ,  Water ;  12 h, 25 °C

Reference

A catalytic N-deacylative alkylation approach to hexahydropyrrolo[2,3-b]indole alkaloids

Kumar, Nivesh; et al, Chemical Communications (Cambridge, 2018, 54(65), 9083-9086

Production Method 4

24424-99-5

73-22-3

82689-19-8

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Methanol ;  30 min, 0 °C; 18 h, 25 °C
1.2 Reagents: Triethylamine Solvents: Dichloromethane ;  24 h, 25 °C
1.3 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  < 0 °C; 4 h, 25 °C

Reference

Design, synthesis, and evaluation of novel Akt1 inhibitors based on an indole scaffold

Yang, Dezhi ; et al, Chemical Biology & Drug Design, 2017, 90(5), 791-803

Production Method 5

24424-99-5

73-22-3

82689-19-8

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Methanol ;  30 min, 0 °C; 18 h, rt
1.2 Reagents: Triethylamine Solvents: Dichloromethane ;  24 h, 25 °C
1.3 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  0 °C; 4 h, rt

Reference

Design, synthesis and evaluation of novel indole derivatives as AKT inhibitors

Yang, Dezhi; et al, Bioorganic & Medicinal Chemistry, 2014, 22(1), 366-373

Production Method 6

24424-99-5

2899-29-8

82689-19-8

Reaction Conditions

1.1 Solvents: 1,4-Dioxane ,  Water ;  3 h, rt

Reference

Pseudosymmetry in Azabicyclo[2.1.1]hexanes. A Stereoselective Construction of the Bicyclic Core of Peduncularine

Ragains, Justin R.; et al, Organic Letters, 2006, 8(20), 4437-4440

Production Method 7

73-22-3

82689-19-8

Reaction Conditions

1.1 Reagents: Thionyl chloride ;  0 °C; overnight, 60 °C
2.1 Reagents: Triethylamine Solvents: Dichloromethane ;  8 h, rt
3.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  4 h, 0 °C
3.2 Reagents: Citric acid Solvents: Water ;  > 1 min

Reference

Development of N-Hydroxycinnamamide-Based Histone Deacetylase Inhibitors with an Indole-Containing Cap Group

Zhang, Yingjie; et al, ACS Medicinal Chemistry Letters, 2013, 4(2), 235-238

Production Method 8

13139-14-5

82689-19-8

Reaction Conditions

1.1 Reagents: 4-Methylmorpholine ,  Isobutyl chloroformate Solvents: Tetrahydrofuran ;  15 min, -15 °C
1.2 Reagents: Sodium borohydride Solvents: Water ;  1 h, -15 °C
1.3 Reagents: Water

Reference

Synthesis and evaluation of chirally defined side chain variants of 7-chloro-4-aminoquinoline to overcome drug resistance in malaria chemotherapy

Dola, Vasantha Rao; et al, Antimicrobial Agents and Chemotherapy, 2017, 61(3),

Production Method 9

13139-14-5

82689-19-8

Reaction Conditions

1.1 Reagents: Lithium chloride ,  Sodium borohydride Solvents: Tetrahydrofuran ;  overnight, rt

Reference

Synthesis and binding properties of guanidinium biscarboxylates

Spaeth, Andreas; et al, Monatshefte fuer Chemie, 2011, 142(12), 1289-1308

Production Method 10

57229-67-1

82689-19-8

Reaction Conditions

1.1 Reagents: Lithium borohydride Catalysts: Methanol Solvents: Tetrahydrofuran ;  45 min, rt; 45 min, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  0 °C

Reference

Copper-Catalyzed Cyclization of Iodo-tryptophans: A Straightforward Synthesis of Pyrroloindoles

Coste, Alexis; et al, Organic Letters, 2008, 10(17), 3841-3844

Production Method 11

42290-63-1

82689-19-8

Reaction Conditions

1.1 Reagents: Iodine ,  Sodium borohydride Solvents: Tetrahydrofuran

Reference

An efficient method for the reduction of N-protected amino acids and peptides to the corresponding alcohols

Naqvi, T.; et al, Journal of Chemical Research, 1999, (7), 424-425

Production Method 12

24424-99-5

7524-52-9

82689-19-8

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dichloromethane ;  8 h, rt
2.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  4 h, 0 °C
2.2 Reagents: Citric acid Solvents: Water ;  > 1 min

Reference

Development of N-Hydroxycinnamamide-Based Histone Deacetylase Inhibitors with an Indole-Containing Cap Group

Zhang, Yingjie; et al, ACS Medicinal Chemistry Letters, 2013, 4(2), 235-238

Production Method 13

73-22-3

82689-19-8

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  4 h, 80 °C; 80 °C → 0 °C
1.2 Reagents: Sodium sulfate Solvents: Water
2.1 Solvents: 1,4-Dioxane ,  Water ;  12 h, 25 °C

Reference

A catalytic N-deacylative alkylation approach to hexahydropyrrolo[2,3-b]indole alkaloids

Kumar, Nivesh; et al, Chemical Communications (Cambridge, 2018, 54(65), 9083-9086

(S)-tert-Butyl (1-Hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate Raw materials

• Di-tert-butyl dicarbonate
• Boc-Trp-OMe
• L-(-)-Tryptophanol
• Nα-Boc-L-tryptophan
• Na-Boc-L-tryptophan benzyl ester
• L-Tryptophan,N-[(1,1-dimethylethoxy)carbonyl]-, pentachlorophenyl ester (9CI)
• L-Tryptophan
• L-tryptophan methyl ester hydrochloride

(S)-tert-Butyl (1-Hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate Preparation Products

• (S)-tert-Butyl (1-Hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate (82689-19-8)

• 1. Excited state characterization of carbonyl containing carotenoids: a comparison between single and multireference descriptions?
  Riccardo Spezia,Stefan Knecht,Benedetta Mennucci Phys. Chem. Chem. Phys., 2017,19, 17156-17166
• 2. Examination of the hydrogen-bonding networks in small water clusters (n = 2–5, 13, 17) using absolutely localized molecular orbital energy decomposition analysis?
  Erika A. Cobar,Paul R. Horn,Robert G. Bergman,Martin Head-Gordon Phys. Chem. Chem. Phys., 2012,14, 15328-15339
• 3. Fe3O4/PEG-SO3H as a heterogeneous and magnetically-recyclable nanocatalyst for the oxidation of sulfides to sulfones or sulfoxides
  Saeideh Mirfakhraei,Malak Hekmati,Fereshteh Hosseini Eshbala,Hojat Veisi New J. Chem., 2018,42, 1757-1761
• 4. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203
• 5. Evolution of cellulose into flexible conductive green electronics: a smart strategy to fabricate sustainable electrodes for supercapacitors
  Tengfei Yu,Yuehan Wu,Wei Li,Bin Li RSC Adv., 2014,4, 34134-34143

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives 3-alkylindoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indoles 3-alkylindoles
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

Comprehensive Guide to (S)-tert-Butyl (1-Hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate (CAS No. 82689-19-8)

(S)-tert-Butyl (1-Hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate (CAS No. 82689-19-8) is a specialized chiral compound widely used in pharmaceutical research and organic synthesis. This compound features a unique indole moiety combined with a tert-butyl carbamate group, making it valuable for drug discovery and asymmetric synthesis. Researchers and manufacturers often seek this compound for its role in developing bioactive molecules, particularly in neurological and oncological studies.

The structural complexity of (S)-tert-Butyl (1-Hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate allows it to serve as a key intermediate in synthesizing peptide-based therapeutics. Its chiral center and hydroxy functional group enable selective modifications, which are crucial for optimizing drug efficacy and reducing side effects. Given the rising demand for precision medicine, this compound has gained attention in the pharmaceutical industry for its potential in targeted therapies.

One of the most searched questions about CAS No. 82689-19-8 is its solubility and stability under different conditions. Studies indicate that this compound exhibits good solubility in polar organic solvents like dimethyl sulfoxide (DMSO) and methanol, making it suitable for laboratory applications. Stability tests show that it remains intact at room temperature when stored in a dry, dark environment, which is critical for long-term research projects.

In recent years, the interest in indole derivatives has surged due to their presence in natural products and FDA-approved drugs. (S)-tert-Butyl (1-Hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate is no exception, as it shares structural similarities with serotonin and melatonin analogs. This connection has led to increased research into its potential applications in treating mood disorders and sleep-related conditions, aligning with the growing focus on mental health therapeutics.

From a synthetic chemistry perspective, the tert-butyl carbamate (Boc) protecting group in this compound is highly advantageous. It provides stability during multi-step reactions while allowing easy deprotection under mild acidic conditions. This feature is particularly useful in solid-phase peptide synthesis (SPPS), a technique widely used in developing novel biologics and vaccines—an area of significant interest post-pandemic.

Market trends indicate a steady demand for CAS No. 82689-19-8, driven by pharmaceutical companies and academic institutions. The compound's versatility in medicinal chemistry and its role in cutting-edge research contribute to its commercial value. Suppliers often highlight its high purity (>98%) and enantiomeric excess (>99%), which are critical parameters for researchers working on chiral drug development.

For those exploring green chemistry alternatives, recent studies have investigated eco-friendly synthesis routes for (S)-tert-Butyl (1-Hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate. These approaches focus on reducing hazardous byproducts and improving atom economy, addressing the pharmaceutical industry's sustainability goals. Such innovations align with global trends toward environmentally conscious research and development.

Quality control is paramount when working with chiral intermediates like this compound. Analytical techniques such as HPLC, NMR, and mass spectrometry are routinely employed to verify its identity and purity. These methods ensure reproducibility in research, a factor that peer-reviewed journals increasingly emphasize in their publication guidelines.

Looking ahead, the applications of (S)-tert-Butyl (1-Hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate may expand into new therapeutic areas. With advances in computational drug design and high-throughput screening, researchers can more efficiently explore its potential in treating rare diseases and antibiotic-resistant infections—topics currently dominating scientific discussions.

In conclusion, CAS No. 82689-19-8 represents an important building block in modern pharmaceutical chemistry. Its unique structural features, combined with growing research interest in indole-containing compounds, position it as a valuable tool for drug discovery. As the scientific community continues to tackle global health challenges, specialized intermediates like this will undoubtedly play a crucial role in developing next-generation therapeutics.

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