Methanol → (R)-3-(3-carboxy-4-methyl-phenyl)-piperidine-1-carboxylic acid 4-trifluoromethyl-benzyl ester

HRID 1269522노트

반응식

HRID 1269522 반응식
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:30]=[CH:29][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([C:24]([O:26]CC)=[O:25])[CH:18]=3)[CH2:12]2)=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].CO>O>[F:31][C:2]([F:1])([F:32])[C:3]1[CH:30]=[CH:29][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([C:24]([OH:26])=[O:25])[CH:18]=3)[CH2:12]2)=[O:10])=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 68885831(R)-3-(3-ethoxycarbonyl-4-methyl-phenyl)-piperidine-1-carboxylic acid 4-trifluoromethyl-benzyl ester

생성물 1

HCID 10454852(R)-3-(3-carboxy-4-methyl-phenyl)-piperidine-1-carboxylic acid 4-trifluoromethyl-benzyl ester수율 99.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of (R)-3-(3-ethoxycarbonyl-4-methyl-phenyl)-piperidine-1-carboxylic acid 4-trifluoromethyl-benzyl ester (2.12 g, 4.72 mmol), potassium carbonate (1.30 g, 9.43 mmol), methanol (25 mL) and water (6 mL) was heated at reflux for 3 h, cooled to room temperature and concentrated under reduced pressure. The resulting residue was taken up in water (150 mL), acidified with 1N aqueous hydrochloric acid and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to yield 1.98 g (99%) (R)-3-(3-carboxy-4-methyl-phenyl)-piperidine-1-carboxylic acid 4-trifluoromethyl-benzyl ester as a white solid.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated under reduced pressure
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. washThe combined organic extracts were washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-55a79ad49d56498e8cf139ee7b8bedd0
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199243B2

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