2-Allyl-3-(allyl-(4-methoxy-benzenesulfonyl)-amino)-succinic acid 1-benzyl ester 4-tert-butyl ester → 1-(4-Methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2,3-dicarboxylic acid 3-benzyl ester 2-tert-butyl ester

HRID 1357789ノート

反応式

HRID 1357789 の反応式
[C:1]([O:5][C:6](=[O:37])[CH:7]([N:22]([CH2:34][CH:35]=[CH2:36])[S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH:8]([CH2:19]C=C)[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2]>ClCCl.[Ru]>[C:1]([O:5][C:6]([CH:7]1[CH:8]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:19][CH:36]=[CH:35][CH2:34][N:22]1[S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)(=[O:24])=[O:25])=[O:37])([CH3:3])([CH3:2])[CH3:4]

参加物

4

反応物 1

HCID 120878652-Allyl-3-(allyl-(4-methoxy-benzenesulfonyl)-amino)-succinic acid 1-benzyl ester 4-tert-butyl ester

生成物 1

HCID 155505221-(4-Methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2,3-dicarboxylic acid 3-benzyl ester 2-tert-butyl ester

試薬・触媒・溶媒 2

HCID 23950Ruthenium触媒HCID 6344Dichloromethane溶媒

実験手順

2-Allyl-3-[allyl-(4-methoxy-benzenesulfonyl)-amino]-succinic acid 1-benzyl ester 4-tert-butyl ester (5.5 g, 10.4 mmol) are solved in 40 ml Dichloromethane and deoxygenated and flushed with Argon three times. The catalyst (RuCl2(PCy3)2=−Ph) (100 mg, 0.12 mmol) is added and the reaction is deoxygenated and flushed with Argon one more time. The reaction solution is stirred for 7 h at room temperature. Another (90 mg, 0.11 mmol) of the Ruthenium catalyst are added and the reaction is stirred over night. Evaporation of the solvent followed by flash-chromatography, Hexane/Ethylacetate (3:1) afforded the product: 1H NMR (CDCl3 400 Mhz), ppm: 7.81 (d, 2H), 7.37 (m, 5H), 6.93 (d, 2H), 5.60 (m, 2H), 5.10 (m, 3H), 4.18 (dd, 1H), 4.05 (dd, 1 H), 3.88 (s, 3H), 3.20 (ddd, 1H), 2.68 (m, 2H), 1.32 (s, 9H).

後処理

  1. customdeoxygenated
  2. customflushed with Argon three times
  3. additionThe catalyst (RuCl2(PCy3)2=−Ph) (100 mg, 0.12 mmol) is added
  4. customthe reaction is deoxygenated
  5. customflushed with Argon one more time
  6. stirringthe reaction is stirred over night
  7. customEvaporation of the solvent
  8. customafforded the product

出典と根拠

ORDレコード
ord-195fa0b3d50847718deb3cbdd3589bb6
出典データセット
uspto-grants-2003_07
特許番号
US06593351B2

反応ノート

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