4-Pyrrolidinopyridine → HCID 18652194, compound

Participants

Reaction Conditions

Reaction Steps

3α-tert-butyldiphenylsilyloxy-17β-[(1,1-diphenyl)-1-penten-4-yl]-12α-hydroxy-5β-androstane (10.6 g), 4-pyrrolidinopyridine (0.207 g) and 2,2-dimethylbutyryl chloride (2.25 g) are dissolved in pyridine (55 ml) and the solution warmed to 110° C., stirred for about 1 hour, additional 2,2-dimethylbutyryl chloride (2.25 g) is added and stirring continued for about 14 hours at 110° C. The mixture is cooled, diluted with 20% ether in hexane and washed with water, then 1M hydrochloric acid. The organic solution is dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by flash chromatography in 10% ether in hexane to give the desired product.

Provenance & Evidence