HCID 12796481, compound → HCID 12796493, compound

HRID 2049492Notes

Reaction equation

HRID 2049492 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([CH3:28])[C@@H:11]([CH2:12][CH2:13]2)[CH2:10][C@H:9]([OH:24])[C@@H:8]([O:25][CH2:26][CH3:27])[CH2:7]1)[CH3:3]>C(OCC)(=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([CH3:28])[C@@H:11]([CH2:12][CH2:13]2)[CH2:10][C@H:9]([OH:24])[C@@H:8]([O:25][CH2:26][CH3:27])[CH2:7]1)[CH3:3]

Participants

4

Reactant 1

HCID 12796481HCID 12796481, compound

Product 1

HCID 12796493HCID 12796493, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(Z)-11α-N,N-Dimethylamino-2β-ethoxy-5α-pregn-17(20)-en-3α-ol (585 mg) in ethyl acetate (22 ml) containing 10% Pd-C (400 mg) was stirred under hydrogen. The catalyst was removed by filtration through Kieselguhr and the solvent evaporated in vacuo. Crystallisation of the residue from aqueous methanol gave the title compound (440 mg), m.p. 57°-59° C., [α]D -4.8°.

Workup

  1. customThe catalyst was removed by filtration through Kieselguhr
  2. customthe solvent evaporated in vacuo
  3. customCrystallisation of the residue from aqueous methanol

Sources & evidence

ORD record
ord-e40255b040e0434bba5f79147bdacf1c
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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