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 1357789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1357789
[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-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).

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-195fa0b3d50847718deb3cbdd3589bb6
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593351B2

Notizen zur Reaktion

Wird geladen…