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

HRID 1867466Notes

Reaction equation

HRID 1867466 reaction equation
[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]

Participants

5

Reactant 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 ester2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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 di-chloromethane, 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.

Workup

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

Sources & evidence

ORD record
ord-3958f3454d0746938ff4ea16df997848
Source dataset
uspto-grants-2009_12
Patent number
US07632844B2

Reaction notes

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