(+)-Hecogenin → Spirostan-3,12-diol

HRID 1779932Notes

Reaction equation

HRID 1779932 reaction equation
[CH3:1][C@@H:2]1[C@:25]2([O:31][CH2:30][C@H:28]([CH3:29])[CH2:27][CH2:26]2)[O:24][C@H:4]2[CH2:5][C@@H:6]3[C@@:20]([CH3:21])([C@@H:3]12)[C:19](=[O:22])[CH2:18][C@H:17]1[C@H:7]3[CH2:8][CH2:9][C@@H:10]2[C@:15]1([CH3:16])[CH2:14][CH2:13][C@H:12]([OH:23])[CH2:11]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH3:1][C@@H:2]1[C@:25]2([O:31][CH2:30][C@H:28]([CH3:29])[CH2:27][CH2:26]2)[O:24][C@H:4]2[CH2:5][C@@H:6]3[C@@:20]([CH3:21])([C@@H:3]12)[C@H:19]([OH:22])[CH2:18][C@H:17]1[C@H:7]3[CH2:8][CH2:9][C@@H:10]2[C@:15]1([CH3:16])[CH2:14][CH2:13][C@H:12]([OH:23])[CH2:11]2

Participants

4

Reactant 2

HCID 91453(+)-HecogeninHCID 21226445Aluminium lithium hydride

Product 1

HCID 167555Spirostan-3,12-diol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Using the procedure described in J. Am. Chem. Soc., 1954, 76, 4013, (3β,5α,25R)-spirostan-3-ol-12-one was reduced with lithium aluminum hydride in ether to give a mixture of C-12 alcohols from which the title compound was isolated.

Workup

  1. customto give

Sources & evidence

ORD record
ord-b66b47d7a90c4f9a92b14dd1b0ce9416
Source dataset
uspto-grants-1997_05
Patent number
US05629295

Reaction notes

Loading…