Nitrogen → HCID 69998310, compound

Participants

Reaction Conditions

Reaction Steps

A 50 mL 2-neck flask equipped with a rubber septum, magnetic stirring bar and N2 inlet was charged with lithium bis(trimethylsilyl)amide (12.9 mL of 1.0M solution, 12.9 mmol). The solution was cooled to -78° C. under N2 in dry ice-acetone bath and anhydrous ethyl acetate (1.2 mL, 12.9 mmol) was added dropwise from a syringe. The reaction was stirred at -78° C. for 30 minutes and then a solution of 3,17-bis(ethylenedioxy)-5-androsten-19-al (1 g, 2.58 mmol) (Lovett, J. A. et al., 1984, J. Med. Chem. 27:734-740) in anhydrous tetrahydrofuran (15 mL) was added dropwise to the solution of the enolate. After completion of the addition, the reaction was stirred for an additional 1.5 hours in the dry ice-acetone bath under nitrogen. The reaction was then quenched with the addition of saturated ammonium chloride solution (~ 30 mL) and the resulting suspension was extracted three times with ethyl acetate (3×25 mL). The combined ethyl acetate extract was washed once with brine (~ 30 mL) and was then dried over magnesium sulfate. After filtration, the solvent was removed under reduced pressure to yield an oil which was used as such in the next reaction: yield 1.67 g (crude); mass spectrum (chemical ionization) m/z 477 (M+H+).

Provenance & Evidence