HCID 86733306, compound → HCID 86733305, compound

HRID 1606372Notes

Reaction equation

HRID 1606372 reaction equation
[OH:1][C@@H:2]1[C@@H:21]([O:22][CH3:23])[CH2:20][C@@:19]2([CH3:24])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:25])[CH2:16][C@@:15]2([CH3:26])[C@H:8]3[CH2:9][C:10]([CH3:27])=[C:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[H][H]>C(OCC)(=O)C.[Pd]>[OH:1][C@@H:2]1[C@@H:21]([O:22][CH3:23])[CH2:20][C@@:19]2([CH3:24])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:25])[CH2:16][C@@:15]2([CH3:26])[C@H:8]3[CH2:9][C@H:10]([CH3:27])[C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1

Participants

5

Reactant 2

HCID 86733306HCID 86733306, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86733305HCID 86733305, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3α-Hydroxy-2β-methoxy-16-methyl-5α-pregn-16-ene-11,20-dione (187 mg.) in ethyl acetate (50 ml.) was hydrogenated over 10% palladium-on-carbon catalyst (60 mg.) at atmospheric pressure for 20 minutes, during which time 11 ml. of hydrogen was taken up. The catalyst was filtered off and the filtrate evaporated to a white foam (190 mg.) which was purified by preparative T.L.C. in ethyl acetate/petrol 3/2, run 3 times, to give 88 mg. of impure product which was purified by preparative T.L.C. in ethyl acetate/benzene (1/1) and recrystallisation from ether/petrol to give title compound (68 mg.) as fine white crystals, m.p. 180°-182°, [α]D + 69.5° (c 0.2).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated to a white foam (190 mg.) which
  3. customwas purified by preparative T.L.C
  4. customto give 88 mg
  5. customof impure product which was purified by preparative T.L.C
  6. customin ethyl acetate/benzene (1/1) and recrystallisation from ether/petrol

Sources & evidence

ORD record
ord-c5197309d91647c5854bd041b8ddb569
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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