Pyridine → 19-t-Butyldimethylsiloxy-4-androstene-3,17-dione

HRID 1390767Notes

Reaction equation

HRID 1390767 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]2.[C:23]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])([CH3:25])[CH3:24].N1C=CC=CC=1>CN(C)C=O>[O:1]([CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]2)[Si:27]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 25237919-Hydroxyandrostenedione

Product 1

HCID 1057397419-t-Butyldimethylsiloxy-4-androstene-3,17-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

19-Hydroxy-4-androstene-3,17-dione, t-butyldimethyl-silylchloride and pyridine are mixed in dry dimethylformamide and heated on a steam bath overnight. The reaction mixture is poured onto water and stirred well for 15 minutes. The resulting solid is filtered and dissolved in methylenechloride, dried over magnesium sulfate and the solvent removed by evaporation. The residue which remains is crystallized from an acetone-hexane solution to yield 19-t-butyldimethylsiloxy-4-androstene-3,17-dione.

Workup

  1. temperatureheated on a steam bath overnight
  2. additionThe reaction mixture is poured onto water
  3. filtrationThe resulting solid is filtered
  4. dissolutiondissolved in methylenechloride
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent removed by evaporation
  7. customThe residue which remains is crystallized from an acetone-hexane solution

Sources & evidence

ORD record
ord-c5cdcb71bc4e488e82be1338f5f0ec98
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

Loading…