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

HRID 256152

反応式

HRID 256152 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 13932937N-(3-phenoxy)propionyl-prolinol収率 91.4%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4d3d561d4b8840baba480f8900cf72fb
出典データセット
uspto-grants-1987_10
特許番号
US04701465

関連ノート

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