Borane → HCID 58610165, compound

Participants

Reaction Conditions

Reaction Steps

A solution of borane in tetrahydrofuran (1M, 29 ml) was added dropwise to a stirred solution of diastereomer 1 (2R)-2-[(S)-(4-chlorophenyl)(hydroxy)methyl]-4-benzylmorpholin-3-one and (2S)-2-[(R)-(4-chlorophenyl)(hydroxy)methyl]-4-benzylmorpholin-3-one (2.40 g 7.24 mmol) in dried tetrahydrofuran (30 ml) at room temperature under nitrogen causing effervesence. The solution was heated to 60° C. for 2 h, allowed to cool to room temperature and excess borane quenched by adding methanol (14 ml) slowly. Aqueous hydrochloric acid (1M, 14 ml) was added, heated to 60° C. for 1 h and then evaporated to a white solid. Added saturated aqueous sodium carbonate (50 ml) and diethyl ether (50 ml) to dissolve the solid and extracted with diethyl ether (2×50ml). The extracts were washed with brine solution, dried, filtered and evaporated to a colourless oil (2.38 g). The oil was purified by chromatography on silica eluting with diethyl ether:hexane 75:25 to give (R)-[4-chlorophenyl][(2R)-4-benzylmorpholin-2-yl]methanol and (S)-[4-chlorophenyl][(2S)-4-benzylmorpholin-2-yl]methanol as a colourless oil (2.08 g)

Provenance & Evidence