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 20432ノート

反応式

HRID 20432 の反応式
[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]

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 68563437HCID 68563437、化合物

生成物 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 ester収率 85%

試薬・触媒・溶媒 2

HCID 24385Nickel Dichloride触媒HCID 887Methanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-cf1cd535a69742338a579dc59fe0dd33
出典データセット
uspto-grants-2010_06
特許番号
US07745438B2

反応ノート

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