Reacción #704355

Ecuación de reacción

diethylazodicarboxylate

dihydrocholesterol

phthalimide

triphenylphosphine

→

3-phthalimidocholestane

Rendimiento 81.3%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONUpon the completion of addition the reaction mixture
2. 2
   ConcentraciónThe reaction mixture was concentrated in vacuo to a residue
3. 3
   workup.DISSOLUTIONThis residue was dissolved in 50 ml hexane/ethyl acetate 95/5
4. 4
   Otroa precipitate formed
5. 5
   FiltraciónThe mixture was filtered
6. 6
   ConcentraciónThe filtrate was concentrated to dryness in vacuo
7. 7
   workup.DISSOLUTIONdissolved in 25 ml of hexane/ethyl acetate 95/5
8. 8
   Otrochromatographed on 200 g silica gel (eluent 2 L hexane/ethyl acetate 95/5

Procedimiento

To a solution of dihydrocholesterol (5.0 g, 12.9 mmol, Aldrich), phthalimide (2.0 g, 13.6 mmol, Aldrich), and triphenylphosphine (3.8 g, 13.6 mmol, Aldrich) in THF (20 ml, Aldrich) stirred at 0° C. under a nitrogen atmosphere was added dropwise diethylazodicarboxylate (2.3 ml, 14.5 mmol, Aldrich). Upon the completion of addition the reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was concentrated in vacuo to a residue. This residue was dissolved in 50 ml hexane/ethyl acetate 95/5 and a precipitate formed. The mixture was filtered. The filtrate was concentrated to dryness in vacuo, dissolved in 25 ml of hexane/ethyl acetate 95/5 and chromatographed on 200 g silica gel (eluent 2 L hexane/ethyl acetate 95/5 then 1 L hexane/ethyl acetate 90/10). A 76% yield of the desired 3-phthalimidocholestane (5.43 g) was obtained.

Fuente