Imidazole → 3-Oxo-17beta-(t-butyldimethylsilyloxymethyl)-4-androstene

HRID 1165506Notes

Reaction equation

HRID 1165506 reaction equation
[O:1]=[C:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[CH2:21][OH:22])=[CH:3]1.N1C=CN=C1.[Si:28](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>CN(C=O)C>[O:1]=[C:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[CH2:21][O:22][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])=[CH:3]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1437761717beta-Hydroxymethyl-4-androsten-3-on

Product 1

HCID 148013303-Oxo-17beta-(t-butyldimethylsilyloxymethyl)-4-androsteneYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-oxo-17β-(hydroxymethyl)-4-androstene (15 g, 0.05 mol) in 200 ml DMF was added 5.8 g (0.085 mol) imidazole followed by 9.7 g (0.065 mol) t-butyldimethylsilyl chloride. The reaction mixture was stirred at room temperature under argon, for 2.5 hours. The reaction mixture was then poured into 250 ml ice water and washed 3 times with ethyl acetate. The combined organic layers were washed twice with cold 5% hydrochloric acid and once each with saturated sodium bicarbonate solution and brine. The organic layer was dried over sodium sulfate and evaporated. Recrystallization from methanol afforded 16.9 g (82%) of 3-oxo-17β-(t-butyldimethylsilyloxymethyl)-4-androstene as a white crystalline solid.

Workup

  1. washwashed 3 times with ethyl acetate
  2. washThe combined organic layers were washed twice with cold 5% hydrochloric acid
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated
  5. customRecrystallization from methanol

Sources & evidence

ORD record
ord-b6220e9e73414c2cbdc0547cba648108
Source dataset
uspto-grants-1990_03
Patent number
US04910226

Reaction notes

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