Ethyl diazoacetate → HCID 15838329, compound

Participants

Reaction Steps

To a solution of 17β-hydroxy-4-methyl-5α-4-azaandrostan-3-one (2.37 g, 7.75 mmole) in methylene chloride (50 ml) was added ethyl diazoacetate (5.5 g, 48 mmole) and rhodium diacetate dimer (50 mg) intermittently in small portions during 60 hours resulting in ca. 35% conversion to product. The mixture was passed through a flash silica gel column eluted with 1.5% MeOH in CH2Cl2 to give the semi-purified product which was repurified via another flash silica gel column eluted with 60-95% EtOAc in hexane to give the title product. (Rf=0.3/EtOAc) mp. 39°-41° C.

Provenance & Evidence