Dimethyl Sulfide → HCID 178468164, compound

Participants

Reaction Conditions

Reaction Steps

A flame dried 250 mL flask was charged with 7.95 g (27.5 mmol) trans-(4-acetyl-cyclohexylmethyl)-carbamic acid benzyl ester, 60 mL anhydrous THF and 2.7 mL (2.7 mmol) 1M (S)-2-methyl-CBS-oxazoborolidine. The mixture was heated to 50° C. then 11 mL (22 mmol) 2M BH3.DMS was added dropwise over 10 minutes; the reaction mixture was stirred for an additional 30 minutes at 50° C. and then cooled. The reaction was quenched with 25 mL MeOH and concentrated to give an oil. The material was diluted with water and extracted with ethyl acetate (3×40 mL). The combined organics were washed with water (1×100 mL), brine (1×100 mL), dried over Na2SO4 and concentrated to give a white solid, which was then chromatographed on silica gel eluted with 50% ethyl acetate/50% hexanes to give 7.0 g of a white solid.

Provenance & Evidence