Dimethyl Sulfoxide → (4S,7S,11aR)-7-tert-butoxycarbonylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic Acid Methyl Ester

HRID 722731ノート

反応式

HRID 722731 の反応式
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11]C=C)[N:6]1[C:14](=[O:27])[CH:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH:17]=[CH2:18])=[O:4].CS(C)=O>ClCCl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[CH3:1][O:2][C:3]([C@H:5]1[N:6]2[C:14](=[O:27])[C@@H:15]([NH:19][C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:16][CH:17]=[CH:18][CH2:11][C@H:7]2[CH2:8][CH2:9][CH2:10]1)=[O:4]

参加物

5

反応物 2

HCID 679Dimethyl SulfoxideHCID 696598096-allyl-1-(2-tert-butoxycarbonylamino-pent-4-enoyl)-piperidine-2-carboxylic Acid Methyl Ester

生成物 1

HCID 69659542(4S,7S,11aR)-7-tert-butoxycarbonylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic Acid Methyl Ester

試薬・触媒・溶媒 2

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

実験手順

6-Allyl-1-(2-tert-butoxycarbonylamino-pent-4-enoyl)-piperidine-2-carboxylic acid methyl ester, 40, (1.0 g, 2.6 mmol) is dissolved in dichloromethane (100 mL). Grubbs catalyst (0.5 g, 0.61 mmol) is added and the mixture is heated at reflux for 24 hours. The reaction is cooled and dimethylsulfoxide (2 mL) is added. After 24 hours, the solution is concentrated to a oil, which is purified over silica (ethyl acetate/hexanes) to afford 680 mg of the desired product. 1H NMR (CDCl3) δ 6.02 (d, J=6.6 Hz,1H), 5.61 (m, 1H), 5.21 (m, 1H), 4.93 (ddd, J=6.6, 6.2, 6.2 Hz, 1H), 4.54 (m, 1H), 3.71 (s, 3H), 2.95 (ddd, J=16.2, 5.9, 5.9 Hz, 1H), 2.63 (ddd, J=17.6, 12.0, 5.5 Hz,1H), 2.42 (ddd, J=16.2, 5.8, 5.1 Hz, 1H), 2.34–2.16 (m, 2H), 1.90–1.58 (m, 5H), 1.48 (s, 9H); 13C NMR δ 173.0, 172.5, 155.6, 129.2, 125.0, 79.9, 52.4, 52.0, 51.2, 50.8, 36.6, 34.5, 30.1, 28.8(3C), 26.4, 16.0.

後処理

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 24 hours
  3. temperatureThe reaction is cooled
  4. concentrationthe solution is concentrated to a oil, which
  5. customis purified over silica (ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-2910b94ab6c3476c9c05e420614e2bd2
出典データセット
uspto-grants-2006_11
特許番号
US07138395B2

反応ノート

読み込み中…