beta-nitrostyrene, (E)- → (1R,2R,3R,4S)-benzyl 4-((ethoxycarbonyl)methyl)-1-acetyl-3-nitro-2-phenylcyclopentanecarboxylate

HRID 407526

反応式

HRID 407526 の反応式
[C:1]([CH:4]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:5][CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:3])[CH3:2].[N+:23](/[CH:26]=[CH:27]/[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([O-:25])=[O:24]>C(OCC)C>[CH2:11]([O:10][C:8]([CH2:7][C@@H:6]1[CH2:5][C@@:4]([C:1](=[O:3])[CH3:2])([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[C@@H:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:26]1[N+:23]([O-:25])=[O:24])=[O:9])[CH3:12]

参加物

4

反応物 2

HCID 5284459beta-nitrostyrene, (E)-HCID 687750396-Benzyl 1-ethyl 5-acetylhex-2-enedioate

生成物 1

HCID 59592083(1R,2R,3R,4S)-benzyl 4-((ethoxycarbonyl)methyl)-1-acetyl-3-nitro-2-phenylcyclopentanecarboxylate収率 91%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a solution of 6-benzyl 1-ethyl 5-acetylhex-2-enedioate 4b (0.3 mmol, 1.0 eq) and 1-((E)-2-nitrovinyl)benzene (0.45 mmol, 1.5 eq) in diethylether (0.4 mL) was added catalyst VI (Q-NH2) (0.045 mmol, 0.15 eq) at room temperature (22° C.). The resulting mixture was stirred vigorously for 16 hours, then the reaction was continued for about 6 hours after removal of the solvent. After the reaction was completed (monitored by TLC and crude NMR), the title product was afforded by flash chromatography over silica gel (Ethyl acetate:Hexane=1:10 to 1:4) in 91% yield.

後処理

  1. waitthe reaction was continued for about 6 hours
  2. customafter removal of the solvent

出典と根拠

ORDレコード
ord-93c4bfc7e5b648bfae5115f166825662
出典データセット
uspto-grants-2014_06
特許番号
US08754252B2

関連ノート

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