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

HRID 1269544
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반응식

HRID 1269544 반응식
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:32]=[CH:31][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:16][CH2:15][CH2:14][CH:13]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([O:24][CH2:25][C:26]([O:28]CC)=[O:27])[CH:18]=3)[CH2:12]2)=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].CO>O>[F:33][C:2]([F:1])([F:34])[C:3]1[CH:32]=[CH:31][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]([O:24][CH2:25][C:26]([OH:28])=[O:27])[CH:18]=3)[CH2:12]2)=[O:10])=[CH:5][CH:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 688836293-(3-Ethoxycarbonylmethoxy-4-methyl-phenyl)-piperidine-1-carboxylic acid 4-trifluoromethyl-benzyl ester

생성물 1

HCID 10003946(S)-3-(3-carboxymethoxy-4-methyl-phenyl)-piperidine-1-carboxylic acid 4-trifluoromethyl-benzyl ester수율 97.5%

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

A mixture of 3-(3-ethoxycarbonylmethoxy-4-methyl-phenyl)-piperidine-1-carboxylic acid 4-trifluoromethyl-benzyl ester (118 mg, 0.25 mmol), potassium carbonate (68 mg, 0.49 mmol), methanol (10 mL) and water (2 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 (50 mL), acidified with 1N aqueous hydrochloric acid and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to yield 110 mg (97%) of (S)-3-(3-carboxymethoxy-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 (2×50 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-8c258cfdcc434b0faa24879562cbed0f
출처 데이터셋
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07199243B2

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