Tigogenin → Spirostan-3-one

HRID 1779945Notes

Reaction equation

HRID 1779945 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][C@H:13]1[CH2:41][O:40][C@@:16]2([O:20][C@H:19]3[CH2:21][C@H:22]4[C@@H:27]5[CH2:28][CH2:29][C@H:30]6[CH2:35][C@@H:34]([OH:36])[CH2:33][CH2:32][C@:31]6([CH3:37])[C@H:26]5[CH2:25][CH2:24][C@:23]4([CH3:38])[C@H:18]3[C@@H:17]2[CH3:39])[CH2:15][CH2:14]1>C(Cl)Cl.CCOCC>[CH3:39][C@@H:17]1[C@:16]2([O:40][CH2:41][C@H:13]([CH3:12])[CH2:14][CH2:15]2)[O:20][C@H:19]2[CH2:21][C@@H:22]3[C@@:23]([CH3:38])([C@@H:18]12)[CH2:24][CH2:25][C@H:26]1[C@H:27]3[CH2:28][CH2:29][C@@H:30]2[C@:31]1([CH3:37])[CH2:32][CH2:33][C:34](=[O:36])[CH2:35]2

Participants

5

Reactant 2

HCID 99516TigogeninHCID 178418287HCID 178418287, compound

Product 1

HCID 101692Spirostan-3-oneYield 90.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (PCC) was added to a mixture of tigogenin (50.00 g, 120.0 mmol), celite (160 g), in CH2Cl2 (1000 mL) at 0° C. The reaction was allowed to come to ambient temperature and was stirred for 5 hours. The reaction was diluted with 1000 4 mL Et2O and was filtered through a silica gel plug. The plug was washed with an additional 6000 mL Et2O. The filtrate was concentrated in vacuo to afford 45.00 g of the title compound (90.4%).

Workup

  1. customto come to ambient temperature
  2. filtrationwas filtered through a silica gel plug
  3. washThe plug was washed with an additional 6000 mL Et2O
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-25ef02d9a8f643eea706534a7df12541
Source dataset
uspto-grants-1997_05
Patent number
US05629295

Reaction notes

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