3alpha-Hydroxy-21-methylene-21-morpholinomethyl-5alpha-pregnane-11,20-dione → 21,21-Dimethyl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 1973722Notes

Reaction equation

HRID 1973722 reaction equation
[OH:1][C@@H:2]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:26]2[C:25](=[O:31])[CH2:24][C@@:23]2([CH3:32])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:22])[C:13](=[CH2:21])[CH2:14]N2CCOCC2)[CH2:3]1>[Pd].C(OCC)(=O)C>[CH3:14][CH:13]([CH3:21])[C:12](=[O:22])[C@@H:11]1[C@:23]2([CH3:32])[C@H:8]([C@H:7]3[C@H:26]([C:25](=[O:31])[CH2:24]2)[C@:27]2([CH3:30])[C@H:4]([CH2:3][C@H:2]([OH:1])[CH2:29][CH2:28]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 867342893alpha-Hydroxy-21-methylene-21-morpholinomethyl-5alpha-pregnane-11,20-dione

Product 1

HCID 2279516721,21-Dimethyl-3alpha-hydroxy-5alpha-pregnane-11,20-dioneYield 44.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3α-Hydroxy-21-methylene-21-morpholinomethyl-5α-pregnane-11,20-dione (500 mg) was hydrogenated over 10% palladium on carbon (50 mg) in ethyl acetate. The catalyst was filtered off and the filtrate evaporated to a white foam. The foam was purified by preparative t.l.c. (ethyl acetate/petrol) to give title compound (180 mg) as a white foam [α]D + 133° (c, 1.02).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated to a white foam
  3. customThe foam was purified by preparative t.l.c

Sources & evidence

ORD record
ord-7fc3257296714cabbb8c6ba4e17dc80b
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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