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

反応式

HRID 229783 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178479819HCID 178479819、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-a3ea2d4def5041b6a36644d1314d6122
出典データセット
uspto-grants-2009_07
特許番号
US07563784B2

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