Potassium Carbonate → 6-Benzyloxycarbonylamino-8-hydroxy-5,6,7,8-tetrahydroquinoline

HRID 1765330노트

반응식

HRID 1765330 반응식
C([O:4][CH:5]1[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8][CH:7]([NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)Cl>[CH2:19]([O:18][C:16]([NH:15][CH:7]1[CH2:6][CH:5]([OH:4])[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8]1)=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 2

HCID 11430Potassium CarbonateHCID 211070758-Acetoxy-6-benzyloxycarbonylamino-5,6,7,8-tetrahydroquinoline

생성물 1

HCID 211070736-Benzyloxycarbonylamino-8-hydroxy-5,6,7,8-tetrahydroquinoline수율 97%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 8-acetoxy-6-benzyloxycarbonylamino-5,6,7,8-tetrahydroquinoline, cis-trans mixture (1.73 g, 5.07 mmol) in methanol (16 mL) at room temperature under nitrogen was added 10% aqueous potassium carbonate solution (8 mL, 5.79 mmol). After 24 h, the reaction mixture was diluted with methylene chloride. The organic layer was washed sequentially with saturated aqueous ammonium chloride solution and brine, dried over anhydrous magnesium sulfate, and evaporated under vacuum to obtain the title compound (1.47 g, 97%). Silica gel chromatography (eluted with 5% methanol in chloroform) provided inefficient separation of the cis and trans isomers. The cis isomer eluted first. Stereochemical assignment was made based on NOE experiments. Cis isomer: 13C NMR (400 MHz, CDCl3) δ 156.3, 155.8, 147.5, 138.0, 136.5, 128.5, 128.1, 123.1, 77.4, 67.5, 66.5, 44.4, 35.0. HPLC/MS [M+H]+, 299.

후처리

  1. washThe organic layer was washed sequentially with saturated aqueous ammonium chloride solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-b02e0bff0acf4a5999e12e3e89752451
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07226942B2

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