Imidazole → HCID 10993121, compound

HRID 440727Notes

Reaction equation

HRID 440727 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH: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.N1C=CN=C1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].O>CN(C)C=O>[Si:27]([O:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH: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:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 5881DehydroepiandrosteroneHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 10993121HCID 10993121, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.0 g of 3β-hydroxyandrost-5-en-17-one (Coffey S. in Rodd's Chemistry of Carbon Compounds, 1970, IID, 257) in 10 ml of dimethylformamide, 1.7 g of imidazole and 1.95 g of t-butyldimethylsilyl chloride were added at 0° C. After 12 hrs the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure to give 1.3 g of crude 3β-tert-butyldimethylsilyloxy-androst-5-en-17-one

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e54988eaa1a642518cc35654a936a3d8
Source dataset
uspto-grants-1996_05
Patent number
US05521167

Reaction notes

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