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Trifluoroacetic acid → methyl {(2S,3R)-2-[4-(trifluoromethyl)phenyl]piperidin-3-yl}acetate

HRID 1942311
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HRID 1942311 반응식
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[C@@H:6]1[C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:26][C:24]([F:25])([F:27])[C:21]1[CH:20]=[CH:19][C:18]([C@@H:6]2[C@@H:5]([CH2:4][C:3]([O:2][CH3:1])=[O:28])[CH2:10][CH2:9][CH2:8][NH:7]2)=[CH:23][CH:22]=1
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참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86639344tert-butyl (2S,3R)-3-(2-methoxy-2-oxoethyl)-2-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate

생성물 1

HCID 86639343methyl {(2S,3R)-2-[4-(trifluoromethyl)phenyl]piperidin-3-yl}acetate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of the resulting tert-butyl (2S,3R)-3-(2-methoxy-2-oxoethyl)-2-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate (2.8 g, 7.0 mmol) in DCM (50 mL) was treated with TFA (2.7 mL, 35 mmol) and stirred at ambient temperature for 16 hours. The reaction mixture was evaporated in vacuo and partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organics were dried over sodium sulfate, filtered and evaporated in vacuo to give methyl {(2S,3R)-2-[4-(trifluoromethyl)phenyl]piperidin-3-yl}acetate. LC/MS (EIMS, M+H)=302.1.

후처리

  1. customThe reaction mixture was evaporated in vacuo
  2. custompartitioned between saturated sodium bicarbonate solution and ethyl acetate
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-3d6945f00f79482f9875ccb3865e03c8
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08389547B2

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