Sodium borohydride → HCID 66918731, compound
Reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C:9](=[O:11])[CH2:8][C@H:7]1[C:12](=[O:19])[NH:13][C:14]1([C:17]#[N:18])[CH2:16][CH2:15]1)=[O:5])[CH3:2].[BH4-].[Na+]>C1COCC1>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH:9]([OH:11])[CH2:8][C@H:7]1[C:12](=[O:19])[NH:13][C:14]1([C:17]#[N:18])[CH2:16][CH2:15]1)=[O:5])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (1R,2R)-2-(1-cyano-cyclopropylcarbamoyl)-4-oxo-cyclopentanecarboxylic acid ethyl ester (0.38 mmol) in THF (2.0 ml) was added at −15° C. sodium borohydride (0.38 mmol) and stirring was continued for 4 h. The mixture was partitioned between 1N aqueous HCl and ethyl acetate, the organic layer was dried, evaporated and the residue chromatographed on silica using ethyl acetate to give (1R,2R)-2-(1-cyano-cyclopropylcarbamoyl)-4-hydroxy-cyclopentanecarboxylic acid ethyl ester as a 2:1 mixture of epimers as a colorless solid. MS: 267.0 (M+H)+.