Imidazole → HCID 14800132, compound

HRID 327932Notes

Reaction equation

HRID 327932 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:17]([CH2:18][CH2:19][C@:3]12[CH3:4])[C@@H:16]1[C@H:11]([CH2:12][C:13](=[O:20])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.N1C=CN=C1.[C:26]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])([CH3:28])[CH3:27].CCCCCC.CCOC(C)=O>CN(C=O)C.O>[Si:30]([O:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:17]([CH2:18][CH2:19][C@:3]12[CH3:4])[C@@H:16]1[C@H:11]([CH2:12][C:13](=[O:20])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 9420217beta-Hydroxy-5alpha-estran-3-oneHCID 21226206Ethyl acetate hexane

Product 1

HCID 14800132HCID 14800132, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

10 g of 17β-hydroxy-5α-estran-3-one was dissolved in 150 ml of DMF. 3.7 g of imidazole were then added and the mixture was cooled to 0° C. 6.5 g of t-butyl dimethyl silyl chloride were added and the mixture was stirred and gradually warmed to room temperature followed by stirring for two days. TLC (hexane/EtOAc (9:1)) revealed that the reaction was complete. The reaction mixture was diluted with water and then extracted with 500 ml of hexane/EtOAc (9:1) (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and evaporated under reduced pressure to produce crude product (14.6 g). The entire crude yield was flash chromatographed with the Aldrich flash chromatography system. The 600 ml column was filled with 7 inches of 230-400 mesh silica gel, eluting with hexane/EtOAc (10: 1). Once the sample was loaded, 30 ml fractions were taken. Fraction numbers 4-13, yielded 14 g of the title compound, m.p. 103°-104° C.

Workup

  1. temperaturegradually warmed to room temperature
  2. stirringby stirring for two days
  3. extractionextracted with 500 ml of hexane/EtOAc (9:1) (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto produce crude product (14.6 g)
  9. customThe entire crude yield
  10. customchromatographed with the Aldrich flash chromatography system
  11. additionThe 600 ml column was filled with 7 inches of 230-400 mesh silica gel
  12. washeluting with hexane/EtOAc (10: 1)

Sources & evidence

ORD record
ord-a76e235ceb7b46c9b0b85faa40129942
Source dataset
uspto-grants-1993_12
Patent number
US05274089

Reaction notes

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