172825-20-6

Basic information

• Product Name: Cyclopentanecarboxylic acid, 2-hydroxy-1-methyl-, methyl ester, (1S-trans)-
• Synonyms: Cyclopentanecarboxylic acid, 2-hydroxy-1-methyl-, methyl ester, (1S-trans)-
• CAS NO: 172825-20-6
• Molecular Formula: C8H14O3
• Molecular Weight: 158.19496
• Product Categories: CARBOXYLICESTER
• Mol File: 172825-20-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclopentanecarboxylic acid, 2-hydroxy-1-methyl-, methyl ester, (1S-trans)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentanecarboxylic acid, 2-hydroxy-1-methyl-, methyl ester, (1S-trans)-(172825-20-6)
• EPA Substance Registry System: Cyclopentanecarboxylic acid, 2-hydroxy-1-methyl-, methyl ester, (1S-trans)-(172825-20-6)

Safety Data

• Hazardous Substances Data: 172825-20-6(Hazardous Substances Data)

Upstream product

• 30680-84-3 methyl 1-methyl-2-oxocyclopentane-1-carboxylate 
• 67-56-1 methanol 
• 124898-89-1 (2S,4aR,7aS)-2-(tert-butyl)-5,6,7,7a-tetrahydro-4a-methylcyclopentadioxin-4(4aH)-one 
• 122331-02-6 (1S,2R)-2-(Methoxycarbonyl)cyclopentan-1-ol 
• 74-88-4 methyl iodide 
• 10472-24-9 methyl 2-oxocyclopentane-1-carboxylate 
• 124898-85-7 (4aR,7aS)-5,6,7,7a-tetrahydrocyclopentadioxin-4(4aH)-one 
• 122249-17-6 S-ethyl (1R,2S)-2-hydroxycyclopentanecarboxylthioate 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 68317-73-7 3-Methyl-1-cyclopenten-3-carbonsaeuremethylester 
• 95864-69-0 4-Methyl-1-cyclopenten-4-carbonsaeuremethylester 
• 162489-18-1 methyl (R)-1-methyl-2-oxocyclopentanecarboxylate 

Relevant articles and documents

Preparation of enantiopure ketones and alcohols containing a quaternary stereocenter through parallel kinetic resolution of β-keto nitriles

Racemic 1-methyl-2-oxocycloalkanecarbonitriles have been subjected to bioreduction by the fungus Mortierella isabellina NRRL 1757 through a parallel kineticresolution process. The u and l alcohols thus obtained (up to >99% ee) were easily separated and oxidized to the R and S ketones, respectively. The process can be then repeated so that both enantiomers of the ketone and two epimers of the alcohol can be obtained in their enantiopure forms.

Chiral Synthesis via Organoboranes. 42. Selective Reductions. 57. Efficient Kinetic Resolution of Representative α-Tertiary Ketones with B-Chlorodiisopinocampheylborane

Kinetic resolution of racemic α-tertiary ketones with 0.5-0.6 molar equiv of B-chlorodiisopinocampheylborane provides the product alcohols in very high diastereomeric and enantiomeric excess, with the unreacted ketone recovered in very high ee.For example, ethyl 1-methyl-2-oxocyclopentane- and cyclohexanecarboxylates are partially reduced to recover the ketone in 91 to >/=99percent ee and the product alcohols in up to 94percent de, with >90percent ee for the major diastereomer.Bicyclic ketones, such as 1-methyl- and 1-ethylnorcamphor, camphor, and camphenilone, are readily resolved to provide the ketone in 92 to >/=99percent ee, with the product alcohol recovered in high de and ee.Dihydrospirooctane-2,2'(3'H)-furan>-3-one is resolved to provide the ketone in >/=99percent ee and the product alcohol in >/=99percent de.In all the cases studied, the R-isomer of the ketone is recovered when dIpc2BCl is used for kinetic resolution, while lIpc2BCl provides the S-ketone.Optimum conditions for obtaining the product alcohol, or the ketone, or both, in very high yields and ee have been established.

Mono- and Dialkylation of Derivatives of (1R,2S)-2-Hydroxycyclopentanecarboxylic Acid and -cyclohexanecarboxylic Acid via Bicyclic Dioxanones: Selective Generation of Three Contiguous Stereogenic Centers on a Cyclohexane Ring

Ethyl (1R,2S)-2-hydroxycyclopentanecarboxylate and -cyclohexanecarboxylate (1a and 2a, respectively) obtained in 40 and 70 percent yield by reduction of 3-oxocyclopentanecarboxylate and cyclohexanecarboxylate, respectively (Scheme 2), with non-fermenting