Cesium carbonate → (+/-)-(2RS,4aRS,10bRS)-6-(4-Butoxy-phenyl)-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydro-phenanthridin-2-ol

HRID 2054430노트

반응식

HRID 2054430 반응식
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:25]3[C:20](=[CH:21][C:22]([O:28][CH3:29])=[C:23]([O:26][CH3:27])[CH:24]=3)[CH:19]3[CH:14]([CH2:15][CH2:16][CH:17]([O:30]C(=O)C)[CH2:18]3)[N:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+]>CO.ClCCl>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:25]3[C:20](=[CH:21][C:22]([O:28][CH3:29])=[C:23]([O:26][CH3:27])[CH:24]=3)[CH:19]3[CH:14]([CH2:15][CH2:16][CH:17]([OH:30])[CH2:18]3)[N:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

5

반응물 2

HCID 10796Cesium carbonateHCID 10433966(+/-)-Acetic acid (2RS,4aRS,10bRS)-6-(4-butoxy-phenyl)-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl ester2회

생성물 1

HCID 10364168(+/-)-(2RS,4aRS,10bRS)-6-(4-Butoxy-phenyl)-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydro-phenanthridin-2-ol수율 83%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

717 mg of (±)-acetic acid (2RS,4aRS,10bRS)-6-(4-butoxy-phenyl)-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl ester (compound 14) are dissolved in 8 ml of methanol and 1 ml of dichloromethane, 259 mg of cesium carbonate are added and the mixture stirred for 19 h. The solvent is removed and the crude product is purified by flash chromatography (silica, ethyl acetate/triethylamine=9:1) to give 540 mg of the title compound as a colorless foam.

후처리

  1. customThe solvent is removed
  2. customthe crude product is purified by flash chromatography (silica, ethyl acetate/triethylamine=9:1)

출처 및 근거

ORD 기록
ord-52accca59d3e400599b47347569b9e7b
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07329676B2

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