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Trifluoromethanesulfonic anhydride → 1,1-Dimethylethyl 4-(6-bromo-1,2-benzisoxazol-3-yl)-1-piperazinecarboxylate

HRID 1988885
ノート
印刷プレビュー

反応式

HRID 1988885 の反応式
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=O)[NH:7][O:8][C:4]=2[CH:3]=1.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[N:27]1([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(N(C(C)C)CC)(C)C>ClCCl.C1CCCCC1.C(#N)C.N1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([N:30]3[CH2:29][CH2:28][N:27]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:32][CH2:31]3)=[N:7][O:8][C:4]=2[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 112296276-bromo-1,2-benzisoxazol-3-ol2 回

生成物 1

HCID 586564881,1-Dimethylethyl 4-(6-bromo-1,2-benzisoxazol-3-yl)-1-piperazinecarboxylate収率 19.5%

試薬・触媒・溶媒 4

HCID 1049
Pyridine
溶媒
HCID 6342Acetonitrile溶媒
HCID 6344Dichloromethane溶媒
HCID 8078Cyclohexane溶媒

実験手順

An ice-bath cooled solution of 6-bromo-1,2-benzisoxazol-3 (2H)-one (Intermediate 24) (0.05 g) and dry pyridine (0.05 ml) in dry dichloromethane (4 ml) was stirred under nitrogen and treated with triflic anhydride (60 μL). The solution was stirred at room temp. for 4 h, diluted with cyclohexane then applied to a Varian Bond-Elut SPE cartridge (silica, 1 g) and eluted with dichloromethane to give a yellow oil. The oil was dissolved in acetonitrile (2 ml) treated with 1,1-dimethylethyl 1-piperazinecarboxylate (0.04 g) and diisopropylethylamine (0.05 ml) then stirred at 70° under nitrogen for 20 h. The cooled reaction mixture was purified on a Varian Bond-Elut SPE cartridge (silica, 5 g) using dichloromethane:methanol to give the title compound as a white solid (0.016 g).

後処理

  1. stirringThe solution was stirred at room temp. for 4 h
  2. washeluted with dichloromethane
  3. customto give a yellow oil
  4. stirringthen stirred at 70° under nitrogen for 20 h
  5. customThe cooled reaction mixture
  6. customwas purified on a Varian Bond-Elut SPE cartridge (silica, 5 g)

出典と根拠

ORDレコード
ord-c336b2c948e247f388a9f28063766767
出典データセット
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07642276B2

反応ノート

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