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

HRID 371826

Reaction equation

HRID 371826 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.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([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:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

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-butyldimethylsilylchloride 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. The residue 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
  7. customThe residue is crystallized from an acetone-hexane solution

Sources & evidence

ORD record
ord-0d06e6505c2c4bc38a1a215cd98f8202
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Linked notes

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