Sodium borohydride → (4-Mercapto-adamantan-1-yl)-carbamic acid benzyl ester

Participants

Reaction Steps

Ketone 10B (100 mg, 0.317 mmol) in 5 ml of absolute MeOH was added NaBH4 (23 mg, 0.62 mmol) in portions at 0° C. The reaction was stirred for 1 h, at which time the solution was carefully quenched with water. The reaction mixture was extracted with EtOAc twice and the organic phases were combined, dried (anhydrous Na2SO4), and concentrated. The crude mixture was purified by column chromatography (0˜10% MeOH in EtOAc) to yield 51 mg of the desired mixture of alcohols 11A LC-MS (ESR): m/z=318 (M+H)+.

Provenance & Evidence