tert-butyl 4-allyl-4-(N-((1-tosyl-1H-indol-4-yl)methyl)acrylamido)piperidine-1-carboxylate → tert-butyl 2-oxo-1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undec-3-ene-9-carboxylate

HRID 41562ノート

反応式

HRID 41562 の反応式
[CH2:1]([C:4]1([N:17]([CH2:22][C:23]2[CH:31]=[CH:30][CH:29]=[C:28]3[C:24]=2[CH:25]=[CH:26][N:27]3[S:32]([C:35]2[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[C:18](=[O:21])C=C)[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]>ClCCl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[O:21]=[C:18]1[CH:3]=[CH:2][CH2:1][C:4]2([CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:6][CH2:5]2)[N:17]1[CH2:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[CH:25]=[CH:26][N:27]2[S:32]([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33]

参加物

4

反応物 1

HCID 67251369tert-butyl 4-allyl-4-(N-((1-tosyl-1H-indol-4-yl)methyl)acrylamido)piperidine-1-carboxylate

生成物 1

HCID 67251858tert-butyl 2-oxo-1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undec-3-ene-9-carboxylate収率 84%

試薬・触媒・溶媒 2

HCID 178425456HCID 178425456、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl 4-allyl-4-(N-((1-tosyl-1H-indol-4-yl)methyl)acrylamido)piperidine-1-carboxylate (0.075 g, 0.13 mmol) in dichloromethane (5.0 mL) was added Grubbs 2nd generation catalyst (0.006 g, 0.006 mmol) under argon and the reaction mixture was stirred at it overnight. The dark brown solution was concentrated under reduced pressure and the crude product was purified by column chromatography (eluent: 25% ethyl acetate in hexane) to yield the title compound as a solid (0.060 g, 84%). [LCMS RtE=0.523 min, [M+H]+=549.8]

後処理

  1. concentrationThe dark brown solution was concentrated under reduced pressure
  2. customthe crude product was purified by column chromatography (eluent: 25% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-e407ce95cc794e2ab0b69b333ca3446e
出典データセット
uspto-grants-2013_09
特許番号
US08530648B2

反応ノート

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