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

HRID 1765330ノート

反応式

HRID 1765330 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b02e0bff0acf4a5999e12e3e89752451
出典データセット
uspto-grants-2007_06
特許番号
US07226942B2

反応ノート

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