Water → (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(3-phenylpropanoyl)-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3-carboxylic acid

HRID 1684564Notes

Reaction equation

HRID 1684564 reaction equation
[CH2:1]([C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]2[C@H:17]3[C@H:27]([CH2:28][CH2:29][C@:12]12[CH3:13])[C@:25]1([CH3:26])[C:20]([CH:21]=[C:22]([C:30]([O:32]C)=[O:31])[CH2:23][CH2:24]1)=[CH:19][CH2:18]3)=[O:10])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].O>CO>[CH2:1]([C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]2[C@H:17]3[C@H:27]([CH2:28][CH2:29][C@:12]12[CH3:13])[C@:25]1([CH3:26])[C:20]([CH:21]=[C:22]([C:30]([OH:32])=[O:31])[CH2:23][CH2:24]1)=[CH:19][CH2:18]3)=[O:10])[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 54148895HCID 54148895, compound

Product 1

HCID 11026423(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(3-phenylpropanoyl)-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 17β-(phenethylcarbonyl)-androsta-3,5-diene-3-carboxylate, K2CO3, water and methanol is heated at reflux for about 5 hours. Acidification followed by conventional workup yields title compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for about 5 hours

Sources & evidence

ORD record
ord-8f4239ecce904ce88bf1ae2b10f896cd
Source dataset
uspto-grants-1997_06
Patent number
US05641765

Reaction notes

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