Methanol → N-(3-phenoxy)propionyl-prolinol

HRID 256152

반응식

HRID 256152 반응식
C[O:2][C:3](=O)[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:19])[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH4-].[Na+].CO.O>C(O)(C)(C)C>[O:12]([CH2:11][CH2:10][C:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@H:4]1[CH2:3][OH:2])=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 13932886N-(3-phenoxy)propionyl-proline methyl ester

생성물 1

HCID 13932937N-(3-phenoxy)propionyl-prolinol수율 91.4%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

A mixture of N-(3-phenoxy)propionyl-proline methyl ester (2.8 g) and sodium borohydride (950 mg) was suspended in tertiary butyl alcohol (40 ml). To the stirred suspension, dry methanol (8 ml) was added dropwise under reflux. Thereafter, the mixture was stirred under reflux for 1 hour. The heated mixture was cooled to room temperature and water (10 ml) was added under cooling with ice. Methanol and tertiary butyl alcohol were distilled off under vacuum and the residue was subjected to extraction with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under vacuum and the resulting crude product was purified by medium-pressure liquid column chromatography on silica gel (solvent: chloroform) to obtain the end compound as an oil (2.3 g).

후처리

  1. temperatureunder reflux
  2. temperatureunder reflux for 1 hour
  3. temperatureunder cooling with ice
  4. distillationMethanol and tertiary butyl alcohol were distilled off under vacuum
  5. extractionthe residue was subjected to extraction with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under vacuum
  9. customthe resulting crude product was purified by medium-pressure liquid column chromatography on silica gel (solvent: chloroform)

출처 및 근거

ORD 기록
ord-4d3d561d4b8840baba480f8900cf72fb
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04701465

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