Sodium triacetoxyborohydride → HCID 86760444, compound

Participants

Reaction Steps

A solution of amine (1f) (115 mg, 0.4 mmol), aldehyde (b) (90 mg, 0.44 mmol) in chloroform/methanol (2.3 ml/0.3 ml) was treated with freshly activated 3 Å molecular sieves and heated to reflux under argon for 8 hours. The cooled mixture was treated with sodium triacetoxyborohydride (130 mg, 0.6 mmol) and stirred for 16 hours at room temperature. The mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic extract was dried and evaporated to give a brown oil. Chromatography on silica eluting with a methanol/ethyl acetate gradient afforded the free base of the title compound as an oil (60 mg, 32%).

Provenance & Evidence