Methanol → 6-(2,6-Dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol

HRID 1050820Notes

Reaction equation

HRID 1050820 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH2:26][CH3:27])=[C:20]([O:23][CH3:24])[CH:21]=3)[CH:16]3[CH:11]([CH2:12][CH2:13][CH:14]([O:28]C(=O)C)[CH2:15]3)[N:10]=2)=[CH:7][CH:6]=[C:5]([O:32][CH3:33])[N:4]=1.CO.C(=O)([O-])[O-].[Cs+].[Cs+]>ClCCl>[CH3:1][O:2][C:3]1[C:8]([C:9]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH2:26][CH3:27])=[C:20]([O:23][CH3:24])[CH:21]=3)[CH:16]3[CH:11]([CH2:12][CH2:13][CH:14]([OH:28])[CH2:15]3)[N:10]=2)=[CH:7][CH:6]=[C:5]([O:32][CH3:33])[N:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10796Cesium carbonateHCID 67023839Acetic acid (2RS,4aRS,10bRS)-6-(2,6-dimethoxy-pyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydro-phenanthridin-2-yl ester

Product 1

HCID 115677836-(2,6-Dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-olYield 59.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

423 mg of acetic acid (2RS,4aRS,10bRS)-6-(2,6-dimethoxy-pyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydro-phenanthridin-2-yl ester (Example 18) dissolved in 1 ml of dichloromethane and 9 ml of methanol are added to 152 mg of cesium carbonate and the solution stirred for 19 h. The reaction mixture is adsorbed to silica gel and purified by flash chromatography to give 229 mg of the title compound as a colourless foam.

Workup

  1. custompurified by flash chromatography

Sources & evidence

ORD record
ord-7fba2819df5540768f9e535148aa3947
Source dataset
uspto-grants-2016_07
Patent number
US09387205B2

Reaction notes

Loading…