Diosgenone → Smilagenone

HRID 2238457Notes

Reaction equation

HRID 2238457 reaction equation
[CH3:1][C@H:2]1[CH2:30][O:29][C@@:5]2([O:9][C@H:8]3[CH2:10][C@H:11]4[C@@H:16]5[CH2:17][CH2:18][C:19]6[C@@:25]([CH3:26])([C@H:15]5[CH2:14][CH2:13][C@:12]4([CH3:27])[C@H:7]3[C@@H:6]2[CH3:28])[CH2:24][CH2:23][C:21](=[O:22])[CH:20]=6)[CH2:4][CH2:3]1>O1CCCC1.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH3:1][C@H:2]1[CH2:30][O:29][C@@:5]2([O:9][C@H:8]3[CH2:10][C@H:11]4[C@@H:16]5[CH2:17][CH2:18][C@@H:19]6[CH2:20][C:21](=[O:22])[CH2:23][CH2:24][C@:25]6([CH3:26])[C@H:15]5[CH2:14][CH2:13][C@:12]4([CH3:27])[C@H:7]3[C@@H:6]2[CH3:28])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 10251134Diosgenone

Product 1

HCID 160498Smilagenone

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Diosgenone (500 g) was dissolved in tetrahydrofuran (THF) (2500 ml) at 40-45° C. and inerted with nitrogen. 5% Pd—BaSO4 (reduced) (100 g) was added; the flask was purged with hydrogen and stirred under an atmosphere of hydrogen for ca. 6.5 hours. The flask was cooled to ambient temperature and the catalyst removed by filtration through a pad of Celite (50 g). The solvent evaporated to yield crude smilagenone as a solid residue.

Workup

  1. customthe flask was purged with hydrogen
  2. customthe catalyst removed by filtration through a pad of Celite (50 g)
  3. customThe solvent evaporated

Sources & evidence

ORD record
ord-ffad5e70dec54256a553e5c2e171942e
Source dataset
uspto-grants-2010_05
Patent number
US07718792B2

Reaction notes

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