Diosgenone → Smilagenone

HRID 2238458Notes

Reaction equation

HRID 2238458 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.[H][H]>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

5

Reactant 2

HCID 10251134DiosgenoneHCID 178418361HCID 178418361, compound

Product 1

HCID 160498SmilagenoneYield 90%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Diosgenone (700 g) was dissolved in tetrahydrofuran (THF) (4500 ml) and inerted with nitrogen. The mixture was treated with activated carbon (35 g) and hydrogenated over 5% Pd—BaSO4 (reduced) (35 g) at 25° C. and 2.5 barg hydrogen. The catalyst was removed by filtration and the mixture concentrated to ca. quarter volume. Water (3000 ml) was added over ca. 30 minutes and the resultant solid filtered. The solid was washed with methanol (560 ml) and dried under vacuum at 40-50° C. to afford smilagenone (630 g, 90%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe mixture concentrated to ca. quarter volume
  3. additionWater (3000 ml) was added over ca. 30 minutes
  4. filtrationthe resultant solid filtered
  5. washThe solid was washed with methanol (560 ml)
  6. customdried under vacuum at 40-50° C.

Sources & evidence

ORD record
ord-90ee0d3ffe7d49c2b53eabb856577f98
Source dataset
uspto-grants-2010_05
Patent number
US07718792B2

Reaction notes

Loading…