Imidazole → HCID 69334501, compound

HRID 1003179Notes

Reaction equation

HRID 1003179 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C@H:18]([OH:27])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[C:33]([Si:37]([CH3:40])([CH3:39])Cl)([CH3:36])([CH3:35])[CH3:34]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C@H:18]([O:27][Si:37]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:40])[CH3:39])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57246794(17alpha)-3-(Benzyloxy)estra-1,3,5(10)-trien-17-ol

Product 1

HCID 69334501HCID 69334501, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-benzyloxyestra-1,3,5(10)-trien-17α-ol (49, 1.45 g, 4.0 mmol) in DMF (5.0 mL) were added imidazole (0.408 g, 6.0 mmol) and tert-butyldimethylchlorosilane (0.784 g, 5.2 mmol) at room temperature. The reaction mixture was stirred for 2 h, and quenched with saturated aqueous NaHCO3 at 0° C., and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and then dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:CHCl3 :EtOAc (50:50:1→20:20:1, v/v) to afford 1.91 g of 50 (100% yield).

Workup

  1. customquenched with saturated aqueous NaHCO3 at 0° C.
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O, saturated aqueous NaCl
  4. dry with materialdried (Na2SO4)
  5. filtrationThe desiccant was filtered
  6. customthe solvent was evaporated at reduced pressure
  7. customThe residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-0235d31be5014d1db67e4ace29f704ac
Source dataset
uspto-grants-2000_04
Patent number
US06046186

Reaction notes

Loading…