3-Oxo-cyclopentanecarboxylic acid methyl ester → Cyclopentanecarboxylic acid, 3-hydroxy-, methyl ester
Reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6]1)=[O:4].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6]1)=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 3-oxo-cyclopentanecarboxylic acid methyl ester (2.0 g, 1.0 eq) was dissolved in methanol (15 mL) and cooled to 0° C. NaBH4 (0.53 g) was added and the mixture was stirred at 0° C. for 30 min. The mixture was quenched with acetic acid (0.5 mL) and the methanol was evaporated. The residue was taken up in ethyl acetate, washed with water, dried and evaporated. Purification by flash chromatography on silica gel with a dichloromethane/ethyl acetate gradient yielded the title compound as mixture of the cis and trans isomers. Colorless liquid, 1.6 g, 78%.
Workup
- customThe mixture was quenched with acetic acid (0.5 mL)
- customthe methanol was evaporated
- washwashed with water
- customdried
- customevaporated
- customPurification by flash chromatography on silica gel with a dichloromethane/ethyl acetate gradient
Sources & evidence
- ORD record
- ord-5f7c9e0b204b4ef5b1d4e2ce97c11d34
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893099B2
Reaction notes
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