Sodium borohydride → HCID 86611579, compound

Participants

Reaction Steps

A solution of 3.15 g (5 mmol) hept-6-enoic acid {(S)-1-[(R)-1-(2-chloro-acetyl)-3-methyl-hept-6-enylcarbamoyl]-ethyl}methyl-amide in 110 ml ethanol is added to a suspension of 378 mg (10 mmol) sodium borohydride in 30 ml ethanol at −78° C. The temperature is kept below −75° C. during the addition and the mixture is stirred for an additional hour. The reaction is quenched with 25 ml 1 M HCl at −78° C. and the mixture is allowed to warm to rt. After evaporation of the ethanol and addition of 50 ml 1 M HCl the mixture is extracted with EtOAc. The organic layer is washed with 1 M HCl and a half-saturated aqueous sodium chloride solution, dried with sodium sulfate and evaporated. Purification by chromatography on silica gel (cyclohexane/EtOAc 70/30 to 50/50) gives the desired product as a brown oil (mixture of diastereomers).

Provenance & Evidence