반응 #48710

반응 방정식

(2R,3S,5R)-2-(2,2-dimethylpropoxy)-5-[(1R,2S)-3-(2-ethylphenyl)-1-hydroxy-2-nitropropyl]-3-methylmorpholine-4-carboxylic acid tert-butyl ester

sodium borohydride

→

desired compound

수율 85.0%

(2R,3S,5R)-5-[(1S,2S)-2-Amino-3-(2-ethylphenyl)-1-hydroxypropyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester

수율 85.0%

용매

methanol

반응 조건

후처리

1. 1
   workup.DISSOLUTIONDissolve
2. 2
   workup.ADDITIONthe mixture of diastereomers
3. 3
   기타from the previous reaction
4. 4
   기타quench with water
5. 5
   기타on the rotary evaporator
6. 6
   workup.ADDITIONAdd more water and saturated aqueous sodium chloride
7. 7
   추출Extract with ethyl acetate
8. 8
   건조dry (sodium sulfate)
9. 9
   여과filter
10. 10
    농축concentrate
11. 11
    기타to give

실험 절차

Dissolve the mixture of diastereomers from the previous reaction containing (2R,3S,5R)-2-(2,2-dimethylpropoxy)-5-[(1R,2S)-3-(2-ethylphenyl)-1-hydroxy-2-nitropropyl]-3-methylmorpholine-4-carboxylic acid tert-butyl ester in dry methanol (12 mL) and add nickel (II) chloride (267 mg, 2.06 mmol). To the resulting suspension, add sodium borohydride (284 mg, 7.5 mmol) portion-wise over 1 minute. After 30 minutes, quench with water and reduce the volume on the rotary evaporator. Add more water and saturated aqueous sodium chloride. Extract with ethyl acetate. Combine the extracts, dry (sodium sulfate), filter and concentrate to give a diastereomeric mixture of amines containing the desired compound as a light brown oil (418 mg, 85%).

출처