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Methanol → Toluene-4-sulfonic acid 4-(6-hydroxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl ester

HRID 397040
ノート
印刷プレビュー

反応式

HRID 397040 の反応式
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]([C:17]1[CH:22]=[CH:21][C:20]([O:23][S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])=[CH:19][CH:18]=1)[N:12]([C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])[CH2:11][CH2:10]2.CO>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]([C:17]1[CH:18]=[CH:19][C:20]([O:23][S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])=[CH:21][CH:22]=1)[N:12]([C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])[CH2:11][CH2:10]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 887MethanolHCID 25134Boron tribromideHCID 86583956Toluene-4-sulfonic acid 4-(6-methoxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl ester

生成物 1

HCID 86583957Toluene-4-sulfonic acid 4-(6-hydroxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl ester収率 134.6%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

反応条件

温度
0 °C

実験手順

A 1M solution of BBr3 in CH2Cl2 (16.2 ml, 16.2 mmol) was added slowly to a solution of toluene-4-sulfonic acid 4-(6-methoxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl ester (7.459 g, 14.8 mmol) in anhydrous CH2Cl2 (500 ml) at 0° C. under N2. After stirring at 0° C. for 1 hr, the reaction mixture was warmed to rt and stirred at rt for 18 hr. MeOH (250 ml) was slowly added with stirring and the resulting solution was concentrated in vacuo to give 9.793 g of brown residue. Purification by flash chromatography, eluting with hexane:EtOAc (7:3) gave 2.764 g (38% yield) of white solid.

後処理

  1. temperaturethe reaction mixture was warmed to rt
  2. stirringstirred at rt for 18 hr
  3. stirringwith stirring
  4. concentrationthe resulting solution was concentrated in vacuo

出典と根拠

ORDレコード
ord-93b12d8eed2842e3b4bc59137fddba72
出典データセット
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06608203B2

反応ノート

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