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 722731노트

반응식

HRID 722731 반응식
[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]

참가 물질

5

반응물 2

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

생성물 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

시약·촉매·용매 2

HCID 178479819HCID 178479819, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2910b94ab6c3476c9c05e420614e2bd2
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138395B2

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