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 1596166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1596166
[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]

Komponenten

4

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23950RutheniumKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Al lyl-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, 1H), 3.88 (s, 3H), 3.20 (ddd, 1H), 2.68 (m, 2H), 1.32 (s, 9H).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1551f37640ee4a53a31e2d9a89b2ce2d
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06291450B1

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