20,20-Ethylenedioxy 2-hydroxymethylene-5alpha-pregnane-3,11-dione → 20,20-Ethylenedioxy-2alpha-methyl-5alpha-pregnane-3,11-dione
Reaction equation
[CH2:1]1[CH2:29][O:28][C:3]([C@@H:5]2[C@:22]3([CH3:23])[C@H:8]([C@H:9]4[C@H:19]([C:20](=[O:24])[CH2:21]3)[C@:17]3([CH3:18])[C@H:12]([CH2:13][C:14](=[O:27])[C:15](=[CH:25]O)[CH2:16]3)[CH2:11][CH2:10]4)[CH2:7][CH2:6]2)([CH3:4])[O:2]1>[Pd].C(OCC)(=O)C>[CH2:29]1[CH2:1][O:2][C:3]([C@@H:5]2[C@:22]3([CH3:23])[C@H:8]([C@H:9]4[C@H:19]([C:20](=[O:24])[CH2:21]3)[C@:17]3([CH3:18])[C@H:12]([CH2:13][C:14](=[O:27])[C@H:15]([CH3:25])[CH2:16]3)[CH2:11][CH2:10]4)[CH2:7][CH2:6]2)([CH3:4])[O:28]1Participants
4
Procedure
A mixture of 20,20-ethylenedioxy-2-hydroxymethylene-5α-pregnane-3,11-dione (6 g.), palladium-on-charcoal (10%, 2.5 g.) and ethyl acetate (250 ml.) was shaken under hydrogen for 51/2 hr. The mixture was then filtered through Kieselguhr and the filtrate was evaporated to dryness (6.1 g.) in vacuo. A portion of the residue (3 g.) was subjected to preparative t.l.c. The less polar fraction (0.59 g.) was crystallised from methanol to give title compound (0.35 g.), m.p. 168°-169°.