Pyridine-2-sulfonic acid allyl-(2-methyl-pent-4enyl)-amide → 3-Methyl-1-(pyridine-2-sulfonyl)-2,3,4,7-tetrahydro-1H-azepine

HRID 229783

Reaktionsgleichung

Reaktionsgleichung von HRID 229783
[CH2:1]([N:4]([CH2:14][CH:15]([CH3:19])[CH2:16][CH:17]=[CH2:18])[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:7])=[O:6])C=C>C(Cl)Cl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[CH3:19][CH:15]1[CH2:16][CH:17]=[CH:18][CH2:1][N:4]([S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)(=[O:6])=[O:7])[CH2:14]1

Komponenten

4

Edukt 1

HCID 11565389Pyridine-2-sulfonic acid allyl-(2-methyl-pent-4enyl)-amide

Produkt 1

HCID 116302233-Methyl-1-(pyridine-2-sulfonyl)-2,3,4,7-tetrahydro-1H-azepineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178479819HCID 178479819, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Pyridine-2-sulfonic acid allyl-(2-methyl-pent-4-enyl)-amide (1.2 g, 4.3 mmol) was diluted in CH2Cl2 (100 ml). After carefully degass by Ar, Grubbs catalyst (0.35 g, 0.43 mmol) was added under Ar protection. The mixture was then refluxed for 2 h before the reaction mixture was concentrated by rotary evaporation. The product was purified by column chromatography (5%-20% EtOAc/hexanes) to give the title compound (0.9 g, 83% yield): MS (M+H+):253.2; 1H-NMR (400 Hz, CDCl3): d=8.70(d, 1H), 8.0-7.75(m, 2H), 7.5 (m, 1H) 5.79-5.60(m, 2H), 4.00(d, 2H), 3.65(dd, 1H), 3.22(dd, 1H), 2.30-2.05(m, 3H), 0.96(d, 3H)

Aufarbeitung

  1. additionwas added under Ar protection
  2. temperatureThe mixture was then refluxed for 2 h before the reaction mixture
  3. concentrationwas concentrated by rotary evaporation
  4. customThe product was purified by column chromatography (5%-20% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a3ea2d4def5041b6a36644d1314d6122
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563784B2

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