Tetrahydrofuran → HCID 69905604, compound

HRID 582523Notes

Reaction equation

HRID 582523 reaction equation
[OH:1][C@@H:2]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:21])[CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH2:3]1.C1COCC1.[H][H]>C(O)C.[Pd]>[OH:1][C@@H:2]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:21])[CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)[CH2:3]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 53994012HCID 53994012, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69905604HCID 69905604, compoundYield 37.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3α-hydroxy-21-(4-pyridylmethylene)-5β-pregnan-20-one (100 mg, 0.245 mmol) in 4 mL each of ethanol and THF containing 20 mg of 5% Pd/C was subjected to hydrogen atmosphere via a balloon, and stirred for 5hours. The catalyst was then filtered off and the solution concentrated in vacuo. The residue was subjected to flash column chromatography eluting with hexane:acetone to give the title compound (38 mg) as a solid; TLC Rf (hexane:acetone 2:1)=0.28.

Workup

  1. filtrationThe catalyst was then filtered off
  2. concentrationthe solution concentrated in vacuo
  3. washeluting with hexane

Sources & evidence

ORD record
ord-b8969751576e41d89b6d11441231d485
Source dataset
uspto-grants-1999_07
Patent number
US05925630

Reaction notes

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