HCID 70583955, compound → HCID 12796485, compound

HRID 2049489Notes

Reaction equation

HRID 2049489 reaction equation
[CH3:1][N:2]([C@@H:4]1[CH2:21][C@@:19]2([CH3:20])[C@@H:15]([CH2:16][CH:17]=[CH:18]2)[C@H:14]2[C@H:5]1[C@:6]1([CH3:26])[C@@H:11]([CH2:12][CH2:13]2)[CH2:10][C@H:9]([OH:22])[C@@H:8]([O:23][CH2:24][CH3:25])[CH2:7]1)[CH3:3]>C(OCC)(=O)C.[Pd]>[CH3:1][N:2]([C@@H:4]1[CH2:21][C@@:19]2([CH3:20])[C@@H:15]([CH2:16][CH2:17][CH2:18]2)[C@H:14]2[C@H:5]1[C@:6]1([CH3:26])[C@@H:11]([CH2:12][CH2:13]2)[CH2:10][C@H:9]([OH:22])[C@@H:8]([O:23][CH2:24][CH3:25])[CH2:7]1)[CH3:3]

Participants

4

Reactant 1

HCID 70583955HCID 70583955, compound

Product 1

HCID 12796485HCID 12796485, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 11α-N,N-dimethylamino-2β-ethoxy-5α-androst-16-en-3α-ol (181 mg) in ethyl acetate (20 ml) containing 10% palladium on charcoal (180 mg) was stirred at room temperature under hydrogen. The catalyst was removed by filtration through Kieselguhr and the solvent was evaporated in vacuo. Purification of the residue by preparative thin layer chromatography over silica (ethyl acetate:petroleum ether 1:1) and crystallization from aqueous methanol yielded the title compound (83 mg), m.p. 54°-59°, [α]D -16.7°.

Workup

  1. customThe catalyst was removed by filtration through Kieselguhr
  2. customthe solvent was evaporated in vacuo
  3. customPurification of the residue by preparative thin layer chromatography
  4. customover silica (ethyl acetate:petroleum ether 1:1) and crystallization from aqueous methanol

Sources & evidence

ORD record
ord-fb812051711a4eecb361ca58eae0dbf5
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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