Imidazole → 4,4-Dimethyl-17beta-tert-butyldimethylsilyloxyandrost-5-en-3-one

HRID 1182873Notes

Reaction equation

HRID 1182873 reaction equation
[CH3:1][C:2]1([CH3:23])[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]1=[CH:4][CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[OH:22].N1C=CN=C1.[Si:29](Cl)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30].O>CN(C=O)C>[CH3:1][C:2]1([CH3:23])[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]1=[CH:4][CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[O:22][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 22415617beta-Hydroxy-4,4-dimethylandrost-5-en-3-one

Product 1

HCID 687291174,4-Dimethyl-17beta-tert-butyldimethylsilyloxyandrost-5-en-3-oneYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4,4-dimethyl-17β-hydroxyandrost-5-en-3-one (3.34 g) in DMF (30 ml), imidazole (1.40 g) and tert-butyldimethylsilyl chloride (3.15 g) were added. After stirring the mixture overnight at RT, water was added, and stirring was continued for 30 min at 0° C. The formed solid was filtered and, after drying, 4,4-dimethyl-17β-tert-butyldimethylsilyloxyandrost-5-en-3-one was obtained (4.0 g, 93% yield).

Workup

  1. additionwere added
  2. stirringstirring
  3. waitwas continued for 30 min at 0° C
  4. filtrationThe formed solid was filtered
  5. customafter drying

Sources & evidence

ORD record
ord-16094f7580d44b2e9ebdb586b50780bf
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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