HCID 53674511, compound → HCID 70585631, compound

HRID 1701450Notes

Reaction equation

HRID 1701450 reaction equation
[CH3:1][C:2]1[C:21]2[C@:16]([CH3:23])([CH2:17][CH2:18][C:19](=[O:22])[CH:20]=2)[C@@H:15]2[C@H:4]([C@H:5]3[C@:12]([CH3:25])([CH2:13][C:14]2=[O:24])[C@@H:8]([C:9](=[O:11])[CH3:10])[CH2:7][CH2:6]3)[CH:3]=1>C(OCC)(=O)C.[Pd]>[CH3:1][C@H:2]1[C@@H:21]2[C@:16]([CH3:23])([CH2:17][CH2:18][C:19](=[O:22])[CH2:20]2)[C@@H:15]2[C@H:4]([C@H:5]3[C@:12]([CH3:25])([CH2:13][C:14]2=[O:24])[C@@H:8]([C:9](=[O:11])[CH3:10])[CH2:7][CH2:6]3)[CH2:3]1

Participants

4

Reactant 1

HCID 53674511HCID 53674511, compound

Product 1

HCID 70585631HCID 70585631, compoundYield 41.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6-Methylpregna-4,6-diene-3,11,20-trione (1.7 g) in ethyl acetate (100 ml) was hydrogenated at atmospheric pressure using 10% palladium on charcoal (500 mg) as catalyst. The catalyst was filtered off and the filtrate evaporated. Crystallisation of the residue from acetonepetroleum ether (b.p. 60°-80°) gave the title compound (720 mg), m.p. 174°-176°, [α]D +106°.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated
  3. customCrystallisation of the residue from acetonepetroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-d33713cc8dbc4ecc82c8e5097fc22a1b
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

Loading…