m-Chloroperbenzoic acid → HCID 9909778, compound

HRID 986949Notes

Reaction equation

HRID 986949 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[C@H:13]1[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12]1)[N:7]=[C:6]2[C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1.ClC1C=CC=C(C(OO)=[O:37])C=1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[C@H:13]1[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12]1)[N+:7]([O-:37])=[C:6]2[C:19]1[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69288439HCID 69288439, compound

Product 1

HCID 9909778HCID 9909778, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mg of (−)-cis-8,9-dimethoxy-6-(4-methanesulfonylphenyl)-1,2,3,4,4a,10b-hexahydrophenanthridine are dissolved in 30 ml of dichloromethane, treated with 340 mg of m-chloroperbenzoic acid with ice-cooling and stirred in an ice bath for 3 h and at RT for 1 h. After removing the solvent under reduced pressure and chromatography on silica gel using ethyl acetate/triethylamine in the ratio 7:1, the title compound is obtained by concentrating the product fractions.

Workup

  1. temperaturecooling
  2. customAfter removing the solvent under reduced pressure and chromatography on silica gel

Sources & evidence

ORD record
ord-321a24a79f2b4113ac0f5950baf65078
Source dataset
uspto-grants-2003_10
Patent number
US06630483B2

Reaction notes

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