tert-Butyl acrylate → 3-{4-[4-(4-Chloro-3-trifluoromethyl-benzyloxy)-phenyl]-piperidin-1-yl}-propionic acid tert-butyl ester

HRID 2100677노트

반응식

HRID 2100677 반응식
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([C:29]([F:32])([F:31])[F:30])[CH:23]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:33]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])(=[O:36])[CH:34]=[CH2:35]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:38]([O:37][C:33](=[O:36])[CH2:34][CH2:35][N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([C:29]([F:31])([F:30])[F:32])[CH:23]=3)=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)([CH3:41])([CH3:40])[CH3:39]

참가 물질

4

반응물 2

HCID 15458tert-Butyl acrylateHCID 688130084-[4-(4-Chloro-3-trifluoromethyl-benzyloxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 688130223-{4-[4-(4-Chloro-3-trifluoromethyl-benzyloxy)-phenyl]-piperidin-1-yl}-propionic acid tert-butyl ester

시약·촉매·용매 1

HCID 21863450Trifluoroacetic acid methylene chloride용매

반응 조건

온도
90 °C

실험 절차

4-[4-(4-Chloro-3-trifluoromethyl-benzyloxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester (1 eq) is dissolved in 10% TFA/DCM and stirred for 30 minutes. After concentration, the residue is re-dissolved in DCM and washed with saturated NaHCO3 and brine. The organic layer is dried over Na2SO4 and concentrated. The residue is then dissolved in MeOH and t-butyl acrylate (2 eq) is added. The resulting solution is heated at 90° C. in microwave for 10 minutes. After concentration, purification by flash column chromatography (80% EtOAc/hexane) gave 3-{4-[4-(4-Chloro-3-trifluoromethyl-benzyloxy)-phenyl]-piperidin-1-yl}-propionic acid tert-butyl ester. [MS: (ES+) 498.2 (M+1)+].

후처리

  1. concentrationAfter concentration
  2. dissolutionthe residue is re-dissolved in DCM
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialThe organic layer is dried over Na2SO4
  5. concentrationconcentrated
  6. dissolutionThe residue is then dissolved in MeOH
  7. concentrationAfter concentration, purification by flash column chromatography (80% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-ea4827422dd7499eb8814aa11b10c838
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572811B2

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