Boron tribromide → N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

HRID 1785970ノート

反応式

HRID 1785970 の反応式
FC1C=CC(C(Cl)=O)=CC=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([C@H:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([C:32](=[O:41])[C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[C@@H:24]([CH3:42])[CH2:23]2)[C:19](=[O:21])[CH3:20])=[CH:14][CH:13]=1.B(Br)(Br)Br>ClCCl>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([C@H:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([C:32](=[O:41])[C:33]3[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=3)[C@@H:24]([CH3:42])[CH2:23]2)[C:19](=[O:21])[CH3:20])=[CH:14][CH:13]=1.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]([C@H:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([C:32](=[O:41])[C:33]3[CH:34]=[CH:35][C:36]([OH:39])=[CH:37][CH:38]=3)[C@@H:24]([CH3:42])[CH2:23]2)[C:19](=[O:21])[CH3:20])=[CH:16][CH:17]=1

参加物

6

反応物 3

HCID 25134Boron tribromideHCID 678794-Fluorobenzoyl chlorideHCID 10343669N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

生成物 2

HCID 10343669N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamideHCID 58859774N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was prepared following general procedure G, substituting 4-methoxybenzoyl chloride for 4-fluorobenzoyl chloride. (2S,4R)-N-(4-chloro-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was dissolved in dichloromethane and a solution of BBr3 (1.0 M in dichloromethane, 10 mL) was added; the reaction was allowed to stir at room temperature for until no starting material remained. The reaction was washed with sat NaHCO3 carefully and brine. The organics were dried over MgSO4, filtered and concentrated down. The residue was purified by Biotage flash chromatography using 100% EtOAc to give (2S,4R)-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide

後処理

  1. washThe reaction was washed with sat NaHCO3 carefully
  2. dry with materialThe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated down
  5. customThe residue was purified by Biotage flash chromatography

出典と根拠

ORDレコード
ord-ac18ee8682d04f73b3a43febaf0c43ce
出典データセット
uspto-grants-2009_03
特許番号
US07504508B2

反応ノート

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