反应详情

温度

-20 °C

Crude (R)-6-cyano-5-hydroxy-3-oxo-N,N-diphenylhexanamide, approximately 0.2mol, is dissolved in tetrahydrofuran (200 mL) and methanol (100 mL) under anitrogen atmosphere. The solution is cooled to -20° C., and a 50% solution of methoxydiethylborane in tetrahydrofuran (105 mL) is added. Thereaction is cooled to -78° C., and sodium borohydride (24 g, 0.63 mol) is added over 30 minutes. The reaction mixture is maintained at -78° C. for 5 hours, allowed to warm to room temperature, and standfor 10 hours under a nitrogen atmosphere. The reaction is quenched by the addition of acetic acid (40 mL) and concentrated by vacuum distillation toan oil. The residue is dissolved with methanol (400 mL), concentrated by vacuum distillation, redissolved with methanol (300 mL), and reconcentrated by vacuum distillation to give a yellow oil. The oil is taken up in ethyl acetate (300 mL) and washed with deionized water (500 mL). The ethyl acetate solution is concentrated by vacuum distillation to give [R-(R*,R,)])-6-cyano-3,5-dihydroxy-N,N-diphenylhexanamide as an oil which is used without further purification. A small sample is purified by column chromatography on flash silica gel (60:40 hexane:ethyl acetate) as an oil.

1. temperatureThereaction is cooled to -78° C.
2. temperatureThe reaction mixture is maintained at -78° C. for 5 hours
3. temperatureto warm to room temperature
4. customstandfor 10 hours
5. customThe reaction is quenched by the addition of acetic acid (40 mL)
6. concentrationconcentrated by vacuum distillation toan oil
7. dissolutionThe residue is dissolved with methanol (400 mL)
8. concentrationconcentrated by vacuum distillation
9. dissolutionredissolved with methanol (300 mL)
10. distillationreconcentrated by vacuum distillation
11. customto give a yellow oil
12. washwashed with deionized water (500 mL)
13. concentrationThe ethyl acetate solution is concentrated by vacuum distillation