5alpha-Androst-7-ene-3-one-17beta-ol → 5alpha-Androst-8(14)-ene-3-one-17beta-ol
Reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C:7](=[CH:8][CH2:9][C@@H:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[OH:21]>C(OCC)(=O)C.[Pd]>[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C:7]([CH2:8][CH2:9][C@@H:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH2:11]4)=[C:6]1[CH2:5][CH2:4][C@@H:3]2[OH:21]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 5α-androst-7-ene-3-one-17β-ol in ethyl acetate is hydrogenated at room temperature and 1 atmosphere over 10% palladium on carbon for 8 hours. Filtration to remove the catalyst and concentration affords 5α-androst-8(14)-ene-3-one-17β-ol.