1-[(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]-4-penten-1-one → (4R*,10aS*)-4-(4-fluorophenyl)-1,3,4,7,8,10a-hexahydro-2H-pyrido[1,2-a]azepin-6-one

HRID 553884노트

반응식

HRID 553884 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][CH2:11][C@@H:10](C=C)[N:9]2[C:16](=[O:21])[CH2:17][CH2:18][CH:19]=[CH2:20])=[CH:4][CH:3]=1>C(Cl)Cl.CC1C=C(C)C(N2[CH-]N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1CCC([PH+](C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[N:9]3[C:16](=[O:21])[CH2:17][CH2:18][CH:19]=[CH:20][C@@H:10]3[CH2:11][CH2:12][CH2:13]2)=[CH:6][CH:7]=1

참가 물질

4

반응물 1

HCID 690774171-[(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]-4-penten-1-one

생성물 1

HCID 69071429(4R*,10aS*)-4-(4-fluorophenyl)-1,3,4,7,8,10a-hexahydro-2H-pyrido[1,2-a]azepin-6-one수율 52.7%

시약·촉매·용매 2

HCID 12045765Benzylidene(dichloro)(1,3-dimesitylimidazolidin-2-id-2-yl)(tricyclohexylphosphoranyl)ruthenium촉매HCID 6344Dichloromethane용매

실험 절차

A solution of 1-[(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]-4-penten-1-one (307 mg) and tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium (IV) dichloride (64 mg) in methylene chloride (150 mL) was heated under reflux for 25 hours. The reaction solution was left to cool to room temperature and then concentrated. The residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=4:1->ethyl acetate) to obtain 146 mg of the title compound. The property values of the compound are as follows.

후처리

  1. temperatureunder reflux for 25 hours
  2. waitThe reaction solution was left
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=4:1->ethyl acetate)

출처 및 근거

ORD 기록
ord-86cd2c099f0847789b3fe901c6072609
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048878B2

반응 노트

불러오는 중…