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

반응식

HRID 229783 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 178479819HCID 178479819, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-a3ea2d4def5041b6a36644d1314d6122
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563784B2

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