HCID 12796477, compound → HCID 12796491, compound

HRID 2049491Notes

Reaction equation

HRID 2049491 reaction equation
[CH3:1][N:2]([C@@H:4]1[CH2:22][C@@:21]2([CH3:23])[C@@H:15]([CH2:16][CH2:17]/[C:18]/2=[CH:19]/[CH3:20])[C@H:14]2[C@H:5]1[C@:6]1([CH3:25])[C@@H:11]([CH2:12][CH2:13]2)[CH2:10][C@H:9]([OH:24])[CH2:8][CH2:7]1)[CH3:3]>C(O)C.[Pd]>[CH3:1][N:2]([C@@H:4]1[CH2:22][C@@:21]2([CH3:23])[C@@H:15]([CH2:16][CH2:17][C@@H:18]2[CH2:19][CH3:20])[C@H:14]2[C@H:5]1[C@:6]1([CH3:25])[C@@H:11]([CH2:12][CH2:13]2)[CH2:10][C@H:9]([OH:24])[CH2:8][CH2:7]1)[CH3:3]

Participants

4

Reactant 1

HCID 12796477HCID 12796477, compound

Product 1

HCID 12796491HCID 12796491, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(Z)-11α-N,N-Dimethylamino-5α-pregn-17(20)-en-3α-ol (750 mg) in ethanol (25 ml) containing 10% Pd-C (511 mg) was stirred under hydrogen for 100 min. The catalyst was removed by filtration through Kieselguhr and the solvent evaporated in vacuo. Purification of the residue by filtration through a plug of silica in ethyl acetate-petroleum ether (2:1) and crystallisation from aqueous methanol gave the title compound (586 mg) m.p. 147°-150°, [α]D -15.0°

Workup

  1. customThe catalyst was removed by filtration through Kieselguhr
  2. customthe solvent evaporated in vacuo
  3. customPurification of the residue
  4. filtrationby filtration
  5. customthrough a plug of silica in ethyl acetate-petroleum ether (2:1) and crystallisation from aqueous methanol

Sources & evidence

ORD record
ord-1eba5c560f5245108f6894d6e635d994
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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