Imidazole → HCID 22211869, compound

HRID 232795Notes

Reaction equation

HRID 232795 reaction equation
[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H: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:11]2=[O:21])[CH2:3]1.CN(C)C=O.N1C=CN=C1.[Si:32](Cl)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]>N1C=CC=CC=1>[Si:32]([O:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H: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:11]2=[O:21])[CH2:3]1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 5879AndrosteroneHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 22211869HCID 22211869, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-20 °C

Procedure

To 3α-hydroxy-5α-androstan-17-one (25.22 g, 290.5 g/mol, 86.8 mmol) dissolved in 65 mL of dry pyridine was added 65 mL of dry dimethylformamide, imidazole (14.77 g, 68.1 g/mol, 217 mmol), and t-butyldimethylsilylchloride (16.36 g, 151 g/mol, 109 mmol), and the reaction was allowed to stand at room temperature for 12 hours. The reaction mixture was then partitioned between 220 mL of water and 220 mL of ethyl acetate and the combined organic layers were washed with water and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and absolute ethanol was added with cooling to -20° C. to give the titled compound (32 g, 91% yield).

Workup

  1. customThe reaction mixture was then partitioned between 220 mL of water and 220 mL of ethyl acetate
  2. washthe combined organic layers were washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed in vacuo and absolute ethanol
  5. additionwas added

Sources & evidence

ORD record
ord-a7ef2d0de4ca41a1987a929a958ba7ec
Source dataset
uspto-grants-1997_01
Patent number
US05591733

Reaction notes

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