Production Method 1

145549-76-4

939768-64-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ,  Tetrahydrofuran ;  rt → 5 °C; 15 min, 5 °C

Reference

Preparation of spiro-cyclic quinazoline derivatives as phosphodiesterase inhibitors and antiviral agents

, World Intellectual Property Organization, , ,

Production Method 2

145549-76-4

939768-64-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ,  Tetrahydrofuran ;  0 °C; 30 min, 0 °C
1.2 Reagents: Water ;  0 °C

Reference

Bifunctional compounds for degrading BTK via ubiquitin proteasome pathway

, World Intellectual Property Organization, , ,

Production Method 3

145549-76-4

939768-64-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ,  Tetrahydrofuran ;  1 h, 0 °C

Reference

Preparation of thienopyrimidine derivatives useful as acetyl-CoA carboxylase inhibitors

, World Intellectual Property Organization, , ,

Production Method 4

145549-76-4

939768-64-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  2 h, -30 °C; 0.5 h, -30 °C
1.2 Reagents: Water ;  cooled
1.3 Reagents: Ammonium chloride Solvents: Water ;  30 min, 0 °C

Reference

Carboxamide compounds as modulators of eukaryotic initiation factor 2 and their preparation

, World Intellectual Property Organization, , ,

Production Method 5

145549-76-4

939768-64-6

Reaction Conditions

1.1 Reagents: Lithium tri-tert-butoxyaluminum hydride Solvents: Tetrahydrofuran ;  3 h, -78 - -60 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  -78 - -60 °C; pH 5 - 6, 0 °C
1.3 Solvents: Ethyl acetate ;  30 min, 0 °C

Reference

Method for synthesis of cis-3-hydroxycyclobutanecarboxylic acid

, China, , ,

Production Method 6

145549-76-4

939768-64-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ,  Tetrahydrofuran ;  0 °C; 1 h, rt

Reference

Preparation of heteroarylpyrimidinone derivatives as acetyl-CoAcarboxylase inhibitors

, World Intellectual Property Organization, , ,

Production Method 7

145549-76-4

939768-64-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ,  Tetrahydrofuran ;  20 min, 0 °C; 2 h, 0 °C

Reference

Preparation of heteroaryldihydropyrimidine derivatives and methods of treating hepatitis B infections

, World Intellectual Property Organization, , ,

Production Method 8

145549-76-4

939768-64-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ,  Tetrahydrofuran ;  0 °C; 30 min, 0 °C
1.2 Reagents: Water ;  0 °C

Reference

Bifunctional compounds for degrading BTK via ubiquitin proteolytic pathway and their preparation

, World Intellectual Property Organization, , ,

Production Method 9

145549-76-4

939768-64-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Ethanol ;  < 30 °C; 2 h, rt

Reference

Novel oxadiazole compounds as agonists or antagonists of S1P family of G protein coupled receptors and their preparation

, United States, , ,

Production Method 10

145549-76-4

939768-64-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Ethanol ;  < 30 °C; 2 h, rt

Reference

Preparation of oxadiazole compounds as S1P receptor agonists and antagonists

, World Intellectual Property Organization, , ,

Production Method 11

145549-76-4

939768-64-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ,  Tetrahydrofuran ;  15 min, 0 °C
1.2 Reagents: Water

Reference

Heterocyclic compounds for inhibiting or degrading ITK, compositions, comprising the same methods of their making and methods of their use

, World Intellectual Property Organization, , ,

Production Method 12

145549-76-4

939768-64-6

Reaction Conditions

1.1 Reagents: Lithium tri-tert-butoxyaluminum hydride Solvents: Tetrahydrofuran ;  -78 - -60 °C; 4 h, -78 - -60 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 5 - 6

Reference

Synthesis of trans-3-hydroxycyclobutylcarboxylic acid from C1-C6 alkyl 3-carbonylcyclobutanecarboylate via reduction, Mitsunobu reaction and hydrolysis

, China, , ,

Production Method 13

939768-64-6

Reaction Conditions

Reference

Preparation of isothiocyanatoalkylbenzene derivatives and analogs for use as N-acylethanolamine hydrolyzing acid amidase inhibitors

, World Intellectual Property Organization, , ,

Production Method 14

145549-76-4

939768-64-6

1311158-43-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ,  Tetrahydrofuran ;  < 10 °C; 1 h, < 10 °C

Reference

Development of a Scalable Synthesis of Oxadiazole Based S1P1 Receptor Agonists

Lukin, Kirill; Kishore, Vimal; Gordon, Thomas, Organic Process Research & Development, 2013, 17(4), 666-671

Production Method 15

145549-76-4

939768-64-6

1311158-43-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  0 °C; 12 h, rt

Reference

3-Fluoroalkyl (CF3, CHF2, CH2F) Cyclobutane-Derived Building Blocks for Medicinal Chemistry: Synthesis and Physicochemical Properties

Demchuk, Oleksandr P.; Bobovskyi, Bohdan V.; Vashchenko, Bohdan V.; Hryshchuk, Oleksandr V.; Skreminskyi, Artem; et al, European Journal of Organic Chemistry, 2023, 26(24),

Production Method 16

145549-76-4

939768-64-6

1311158-43-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  2 h, -30 °C; 0.5 h, -30 °C
1.2 Reagents: Ammonium chloride Solvents: Water ;  30 min, 0 °C

Reference

Preparation of substituted 1-heteroaryl-bicyclo[1.1.1]pentanyl]acetamides as eukaryotic initiation factor 2B modulators

, World Intellectual Property Organization, , ,

tert-butyl cis-3-hydroxycyclobutanecarboxylate Raw materials

• Tert-Butyl 3-oxocyclobutanecarboxylate

tert-butyl cis-3-hydroxycyclobutanecarboxylate Preparation Products

• tert-butyl cis-3-hydroxycyclobutanecarboxylate (939768-64-6)
• tert-butyl trans-3-hydroxycyclobutanecarboxylate (1311158-43-6)

• 1. Enantio- & chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330
  Sowmyalakshmi Venkataraman RSC Adv., 2015,5, 73807-73813
• 2. Excitation dependent bidirectional electron transfer in phthalocyanine-functionalised MoS2 nanosheets?
  Christopher J. Harrison,Kyle J. Berean,Enrico Della Gaspera,Jian Zhen Ou,Richard B. Kaner,Kourosh Kalantar-zadeh,Torben Daeneke Nanoscale, 2016,8, 16276-16283
• 3. Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage?
  M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. Kaskel J. Mater. Chem. A, 2015,3, 17983-17990
• 4. Excellent humidity sensor based on ultrathin HKUST-1 nanosheets?
  Qiaoe Wang,Meiling Lian,Xiaowen Zhu,Xu Chen RSC Adv., 2021,11, 192-197
• 5. Fc microparticles can modulate the physical extent and magnitude of complement activity?
  David White,Sean R. Stowell Biomater. Sci., 2017,5, 463-474

Comprehensive Overview of tert-butyl cis-3-hydroxycyclobutanecarboxylate (CAS No. 939768-64-6): Properties, Applications, and Industry Insights

In the realm of fine chemicals and pharmaceutical intermediates, tert-butyl cis-3-hydroxycyclobutanecarboxylate (CAS 939768-64-6) has garnered significant attention for its unique structural features and versatile applications. This compound, characterized by its cyclobutane ring and ester functionality, serves as a critical building block in organic synthesis, particularly in the development of bioactive molecules. With the growing demand for chiral synthons and sterically hindered esters, this compound aligns perfectly with modern trends in green chemistry and atom-economical synthesis.

The molecular structure of tert-butyl cis-3-hydroxycyclobutanecarboxylate features a cis-configuration hydroxyl group at the 3-position of the cyclobutane ring, which imparts distinct stereochemical properties. This makes it invaluable for asymmetric catalysis and the construction of complex natural products. Researchers frequently highlight its role in peptide mimetics and small-molecule drug candidates, addressing trending topics like targeted drug delivery and enzyme inhibition.

From a synthetic perspective, the tert-butyl ester group in CAS 939768-64-6 offers exceptional stability under acidic conditions, a property highly sought after in multi-step organic reactions. This aligns with frequent search queries such as "protecting groups for carboxylic acids" and "stable ester derivatives." Moreover, the compound’s hydroxycyclobutane core resonates with current interests in ring-strained systems for bioorthogonal chemistry and PET tracer development.

Industrial applications of tert-butyl cis-3-hydroxycyclobutanecarboxylate span pharmaceutical manufacturing, where it acts as a precursor for kinase inhibitors and GPCR modulators. Its compatibility with flow chemistry and continuous processing—hot topics in process optimization—further enhances its appeal. Analytical techniques like HPLC purity analysis and chiral separation methods are often employed to ensure its quality, addressing common questions about "how to characterize cyclobutane derivatives."

Environmental and regulatory considerations also play a role in its adoption. The compound’s low ecotoxicity profile and compliance with REACH guidelines make it suitable for sustainable workflows. This responds to growing searches for "eco-friendly synthetic intermediates" and "green alternatives in medicinal chemistry."

In summary, tert-butyl cis-3-hydroxycyclobutanecarboxylate (CAS 939768-64-6) exemplifies innovation at the intersection of structural complexity and practical utility. Its relevance to drug discovery, material science, and catalysis research ensures its continued prominence in scientific literature and industrial pipelines alike.

• 87661-19-6(Tert-butyl cyclobutanecarboxylate)
• 85698-82-4(Butanedioic acid, [3-(acetyloxy)-2,3-dimethylbutyl]-, diethyl ester)
• 103245-47-2(NONANOIC ACID, 5-HYDROXY-2-METHYL-, 1,1-DIMETHYLETHYL ESTER, (R*,R*)-)
• 1311166-10-5(tert-butyl 3-hydroxycyclobutanecarboxylate)
• 5238-28-8(Pentanoic acid, 2-methyl-, 1,1-diethylpropyl ester)
• 108836-34-6(1,2-Cyclobutanedicarboxylic acid, bis(1,1-dimethylethyl) ester, trans-)
• 65923-75-3(HEXANEDIOIC ACID, 2,5-DIMETHYL-, BIS(TRIMETHYLHEPTYL) ESTER)
• 1311158-43-6(tert-butyl trans-3-hydroxycyclobutanecarboxylate)
• 108836-33-5(cis-Di-tert-butyl cyclobutane-1,2-dicarboxylate)
• 105598-58-1(3-Oxabicyclo[3.2.0]heptan-2-one, 4,4-dimethyl-)