Sodium borohydride → (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

HRID 20432노트

반응식

HRID 20432 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:28])[C@@H:15]([N+:25]([O-])=O)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][CH3:24])[CH2:12][O:11][C@@H:10]([O:29][CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C@@H:9]1[CH3:35])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.[Ni](Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:28])[C@@H:15]([NH2:25])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][CH3:24])[CH2:12][O:11][C@@H:10]([O:29][CH2:30][C:31]([CH3:32])([CH3:34])[CH3:33])[C@@H:9]1[CH3:35])=[O:7])([CH3:3])([CH3:4])[CH3:2]

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 68563437HCID 68563437, 화합물

생성물 1

HCID 68560674(2R,3S,5R)-5-[(1S,2S)-2-Amino-3-(2-ethylphenyl)-1-hydroxypropyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester수율 85%

시약·촉매·용매 2

HCID 24385Nickel Dichloride촉매HCID 887Methanol용매

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%).

후처리

  1. dissolutionDissolve
  2. additionthe mixture of diastereomers
  3. customfrom the previous reaction
  4. customquench with water
  5. customon the rotary evaporator
  6. additionAdd more water and saturated aqueous sodium chloride
  7. extractionExtract with ethyl acetate
  8. dry with materialdry (sodium sulfate)
  9. filtrationfilter
  10. concentrationconcentrate
  11. customto give

출처 및 근거

ORD 기록
ord-cf1cd535a69742338a579dc59fe0dd33
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745438B2

반응 노트

불러오는 중…