Methyl 2-(3,5-bis(trifluoromethyl)phenyl)-2-diazoacetate → (1R*,2R*,5R*)-8-Benzyl-2-{(1S*)-1-[3,5-bis(trifluoromethyl)phenyl]-(methoxycarbonyl)methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane

HRID 2088165

반응식

HRID 2088165 반응식
[N+](=[C:3]([C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=1)[C:4]([O:6][CH3:7])=[O:5])=[N-].[CH2:22]([N:29]1[C@@H:34]2[CH2:35][CH2:36][C@@:30]1([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C@H:31]([OH:37])[CH2:32][CH2:33]2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1C=CC=CC=1.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[CH2:22]([N:29]1[C@@H:34]2[CH2:35][CH2:36][C@@:30]1([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C@H:31]([O:37][C@H:3]([C:4]([O:6][CH3:7])=[O:5])[C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=1)[CH2:32][CH2:33]2)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

5

반응물 2

HCID 54200568Methyl 2-(3,5-bis(trifluoromethyl)phenyl)-2-diazoacetateHCID 69688994(1R*,2R*,5R*)-8-Benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol

생성물 1

HCID 86586700(1R*,2R*,5R*)-8-Benzyl-2-{(1S*)-1-[3,5-bis(trifluoromethyl)phenyl]-(methoxycarbonyl)methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane

시약·촉매·용매 2

HCID 168478Rhodium acetate촉매HCID 241Benzene용매2회

실험 절차

Slow addition of methyl 2-diazo-2-(3,5-bis(trifluoromethyl)phenyl)acetate (504 mg, 1.61 mmol) as a solution in benzene (3 ml) to (1R*,2R*,5R*)-8-benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol (Description 9; 430 mg, 1.47 mmol) in benzene (3 ml) was carried out in the presence of catalytic rhodium acetate (5 mg) at reflux under N2. The reaction mixture was concentrated in vacuo to give a green oil then purified by flash column chromatography [15% ethyl acetate in iso-hexane] to give the title compound as a yellow oil (mainly 1 isomer)(735 mg, 87%).

후처리

  1. temperatureat reflux under N2
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give a green oil
  4. customthen purified by flash column chromatography [15% ethyl acetate in iso-hexane]

출처 및 근거

ORD 기록
ord-75968bcb1d1949dcb7cde7fe288eb8f2
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06727249B2

연결된 노트

불러오는 중…