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

HRID 2100677ノート

反応式

HRID 2100677 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21863450Trifluoroacetic acid methylene chloride溶媒

反応条件

温度
90 °C

実験手順

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)+].

後処理

  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)

出典と根拠

ORDレコード
ord-ea4827422dd7499eb8814aa11b10c838
出典データセット
uspto-grants-2009_08
特許番号
US07572811B2

反応ノート

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