Potassium Hydroxide → HCID 136333712, compound

HRID 365407Notes

Reaction equation

HRID 365407 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:24]3[C:19](=[CH:20][C:21]([O:28][CH2:29][CH3:30])=[C:22]([O:25][CH2:26][CH3:27])[CH:23]=3)[C@H:18]3[C@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]3)[N:12]=2)=[CH:7][CH:6]=1)(=O)C.[OH-].[K+]>CO>[CH2:26]([O:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[O:28][CH2:29][CH3:30])[C@H:18]1[C@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]1)[N:12]=[C:11]2[C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=1)[CH3:27]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86755882HCID 86755882, compound

Product 1

HCID 136333712HCID 136333712, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.68 g of (+/-)-cis-6-(4-acetoxyphenyl)-8,9-diethoxy-1,2,3,4,4a,10b-hexahydrophenanthridine are dissolved in 15 ml of methanol, treated with 1.1 g of potassium hydroxide and the mixture is stirred at RT for 2 h. After removal of the solvent in vacuo, the residue is taken up in water, rendered neutral and extracted with ethyl acetate. The organic phase is dried using sodium sulfate and the solvent is removed in vacuo. 1.23 g (51.2% of theory) of the title compound of m.p. 232-234° C. are obtained.

Workup

  1. customAfter removal of the solvent in vacuo
  2. extractionextracted with ethyl acetate
  3. customThe organic phase is dried
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-3125ba59bcad482eb6f937423e017bb0
Source dataset
uspto-grants-2000_10
Patent number
US06127378

Reaction notes

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