402587-14-8

Basic information

• Product Name: (+)-ETHYL (S)-2-HYDROXY-4-CYCLOHEXYLBUTYRATE
• Synonyms: (+)-ETHYL (S)-2-HYDROXY-4-CYCLOHEXYLBUTYRATE
• CAS NO: 402587-14-8
• Molecular Formula: C12H22O3
• Molecular Weight: 214.3
• Product Categories: Chiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 402587-14-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Refractive Index: n20/D 1.462
• CAS DataBase Reference: (+)-ETHYL (S)-2-HYDROXY-4-CYCLOHEXYLBUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-ETHYL (S)-2-HYDROXY-4-CYCLOHEXYLBUTYRATE(402587-14-8)
• EPA Substance Registry System: (+)-ETHYL (S)-2-HYDROXY-4-CYCLOHEXYLBUTYRATE(402587-14-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 402587-14-8(Hazardous Substances Data)

Upstream product

• 244277-48-3 ethyl (R)-(-)-2-hydroxy-4-oxo-4-phenylbutanoate 
• 88330-79-4 ethyl-(Z)-2-hydroxy-4-oxo-4-phenyl-but-2-enoate 
• 90315-82-5 ethyl (R)-2-hydroxy-4-phenylbutyrate 
• 243658-52-8 (2S)-2-hydroxy-4-oxo-4-phenyl-butyric acid ethyl ester 
• 125639-64-7 (S)-ethyl 2-hydroxy-4-phenylbutyrate 
• 17851-38-6 ethyl 4-cyclohexylbutanoate 

Relevant articles and documents

Ethyl 2,4-dioxo-4-phenylbutyrate: A versatile intermediate for the large-scale preparation of enantiomerically pure α-hydroxy and α-amino acid esters

Starting from ethyl 2,4-dioxo-4-phenylbutyrate, both enantiomers of six enantiomerically pure α-hydroxy and α-amino acid esters (homophenylalanine derivatives) were prepared on >100 g scale. The key step involves a Pt-cinchona catalyzed enantioselective hydrogenation followed by enrichment via crystallization. All derivatives are commercially available.

Catalytic Hydrogenation of Chiral α-Amino and α-Hydroxy Esters at Room Temperature with Nishimura Catalyst without Racemization

The hydrogenation of carboxylic acid derivatives at room temperature was investigated. With a mixed Rh/Pt oxide (Nishimura catalyst), low to medium activity was observed for various α-amino and α-hydroxy esters. At 100 bar hydrogen pressure and 10% catalysts loading, high yields of the desired amino alcohols and diols were obtained without racemization. The most suitable α-substituents were NH2, NHR, and OH, whereas β-NH2 were less effective. Usually, aromatic rings were also hydrogenated, but with the free bases of amino acids as substrates, some selectivity was observed. No reaction was found for α-NR2, α-OR, and unfunctionalized esters; acids and amides were also not reduced under these conditions. A working hypothesis for the mode of action of the catalyst is presented.