Sodium borohydride → HCID 14796009, compound

Participants

Reaction Steps

The product from part (c) (2.73 g., 8.07 mmole) is dissolved in absolute ethanol (50 ml.) and cooled to 5°. Sodium borohydride (0.6 g., 16.14 mmole) is added portionwise and the reaction mixture is stirred for one hour, diluted with ether (200 ml.), and quenched with 1N HCl to pH 1. The organic layer is separated, washed twice with water and brine, dried (MgSO4), and concentrated in vacuo. The two isomers are separated by flash chromatography on silica gel (Merck, 300 g.) eluting with ethyl acetate:hexane (3:8). The slower moving isomer is identified as the S,S configuration and the faster moving isomer is identified as (1S,2R)-[1-(cyclohexylmethyl)-2-hydroxy-2-(2-thiazolyl)ethyl]carbamic acid, 1,1-dimethylethyl ester; [α]D =-30.72° (c=0.55, methanol). TLC (silica gel; ethyl acetate:hexane; 1:1) Rf =0.70.

Provenance & Evidence