تفاعل #575282

معادلة التفاعل

methoxydiethylborane

(R)-6-cyano-5-hydroxy-3-oxo-N,N-diphenylhexanamide

methanol

sodium borohydride

→

6-cyano-3,5-dihydroxy-N,N-diphenylhexanamide

المذيبات

tetrahydrofuran

ethyl acetate

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction is cooled to -78° C.
2. 2
   درجة الحرارةThe reaction mixture is maintained at -78° C. for 5 hours
3. 3
   درجة الحرارةto warm to room temperature
4. 4
   أخرىThe reaction is quenched by the addition of acetic acid (40 mL)
5. 5
   تركيزconcentrated by vacuum distillation to an oil
6. 6
   workup.DISSOLUTIONThe residue is dissolved with methanol (400 mL)
7. 7
   تركيزconcentrated by vacuum distillation
8. 8
   workup.DISSOLUTIONredissolved with methanol (300 mL)
9. 9
   workup.DISTILLATIONreconcentrated by vacuum distillation
10. 10
    أخرىto give a yellow oil
11. 11
    غسيلwashed with deionized water (500 mL)
12. 12
    تركيزThe ethyl acetate solution is concentrated by vacuum distillation

الإجراء التجريبي

Crude (R)-6-cyano-5-hydroxy-3-oxo-N,N-diphenylhexanamide, approximately 0.2 mol, is dissolved in tetrahydrofuran (200 mL) and methanol (100 mL) under a nitrogen atmosphere. The solution is cooled to -20° C., and a 50% solution of methoxydiethylborane in tetrahydrofuran (105 mL) is added. The reaction 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 stand for 10 hours under a nitrogen atmosphere. The reaction is quenched by the addition of acetic acid (40 mL) and concentrated by vacuum distillation to an 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.

المصدر