Smilagenone → Smilagenin

HRID 2238456Notes

Reaction equation

HRID 2238456 reaction equation
CCC(C)[BH-](C(C)CC)C(C)CC.[Na+].[CH3:15][C@H:16]1[CH2:44][O:43][C@@:19]2([O:23][C@H:22]3[CH2:24][C@H:25]4[C@@H:30]5[CH2:31][CH2:32][C@@H:33]6[CH2:39][C:37](=[O:38])[CH2:36][CH2:35][C@:34]6([CH3:40])[C@H:29]5[CH2:28][CH2:27][C@:26]4([CH3:41])[C@H:21]3[C@@H:20]2[CH3:42])[CH2:18][CH2:17]1>C1COCC1>[CH3:15][C@H:16]1[CH2:44][O:43][C@@:19]2([O:23][C@H:22]3[CH2:24][C@H:25]4[C@@H:30]5[CH2:31][CH2:32][C@@H:33]6[CH2:39][C@@H:37]([OH:38])[CH2:36][CH2:35][C@:34]6([CH3:40])[C@H:29]5[CH2:28][CH2:27][C@:26]4([CH3:41])[C@H:21]3[C@@H:20]2[CH3:42])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 160498SmilagenoneHCID 5129077N-Selectride®

Product 1

HCID 91439SmilageninYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-Selectride® (0.64 ml, 1M in THF) was added to a solution of smilagenone (206 mg) in THF (10 ml) over 10 minutes at −78° C. The mixture was stirred and quenched with 10% aqueous citric acid (2 g in 20 ml water) and the product extracted into DCM (2×50 ml), dried (MgSO4) and evaporated to a colourless oil. The oil was taken up in acetone (20 ml) and water (50 ml) added. The precipitate was collected by filtration and dried to afford smilagenin (200 mg, 97%).

Workup

  1. customquenched with 10% aqueous citric acid (2 g in 20 ml water)
  2. extractionthe product extracted into DCM (2×50 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated to a colourless oil
  5. additionwater (50 ml) added
  6. filtrationThe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-6796220416b64e96be1bc641f20c52ab
Source dataset
uspto-grants-2010_05
Patent number
US07718792B2

Reaction notes

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