20,20-Ethylenedioxy 2-hydroxymethylene-5alpha-pregnane-3,11-dione → 20,20-Ethylenedioxy-2alpha-methyl-5alpha-pregnane-3,11-dione

HRID 1606486Notes

Reaction equation

HRID 1606486 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]1

Participants

4

Reactant 1

HCID 8673333120,20-Ethylenedioxy 2-hydroxymethylene-5alpha-pregnane-3,11-dione

Product 1

HCID 8673333020,20-Ethylenedioxy-2alpha-methyl-5alpha-pregnane-3,11-dioneYield 6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

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°.

Workup

  1. filtrationThe mixture was then filtered through Kieselguhr
  2. customthe filtrate was evaporated to dryness (6.1 g.) in vacuo
  3. customThe less polar fraction (0.59 g.) was crystallised from methanol

Sources & evidence

ORD record
ord-02bf4e31309d4f19a243a96a3cadcfa5
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

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