Sodium cyanoborohydride → HCID 24857670, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ketone 5 (350 mg, 1.202 mmol) in THF (18 mL) and methanol (24 mL) was added methylamine hydrochloride (980 mg, 10 eq). After the solid dissolved, sodium cyanoborohydride (6.0 mL, 1 M in THF, 5 eq) was added in one portion. The mixture was heated in a 50° C. oil bath overnight before being quenched with aqueous sodium bicarbonate and extracted with MTBE. The combined organic layer was washed with brine and evaporated to give a brown-green oil. The oil was dissolved in MTBE and extracted into 10% aqueous hydrochloric acid. The aqueous layer was basicified with KOH and extracted with MTBE. The volatile components were removed in vacuo and the crude green oil was separated on silica gel to give the methylamine (0.20 g, 54%) as a pale-green oil.

Provenance & Evidence