反应详情

温度

60 °C

A solution of borane in tetrahydrofuran (1M, 30.7 ml) was added dropwise to a stirred solution of diastereomer 1 (2R)-2-[(S)-(3-fluorophenyl)(hydroxy)methyl]-4-benzylmorpholin-3-one and (2S)-2-[(R)-(3-fluorophenyl)(hydroxy)methyl]-4-benzylmorpholin-3-one (2.42 g 7.68 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 (15 ml) slowly. Aqueous hydrochloric acid (1M, 15 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 (2×50 ml). 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)-[3-fluorophenyl][(2R)-4-benzylmorpholin-2-yl]methanol and (S)-[3-fluorophenyl][(2S)-4-benzylmorpholin-2-yl]methanol as a colourless oil (2.23 g)

1. temperatureto cool to room temperature
2. customexcess borane quenched
3. additionby adding methanol (15 ml) slowly
4. additionAqueous hydrochloric acid (1M, 15 ml) was added
5. temperatureheated to 60° C. for 1 h
6. customevaporated to a white solid
7. dissolutionAdded saturated aqueous sodium carbonate (50 ml) and diethyl ether (50 ml) to dissolve the solid
8. extractionextracted with diethyl ether (2×50 ml)
9. washThe extracts were washed with brine solution
10. customdried
11. filtrationfiltered
12. customevaporated to a colourless oil (2.38 g)
13. customThe oil was purified by chromatography on silica eluting with diethyl ether:hexane 75:25