Nitrogen → HCID 69998310, compound

Temperature

-78 °C

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+).

1. additionAfter completion of the addition
2. customThe reaction was then quenched with the addition of saturated ammonium chloride solution (~ 30 mL)
3. extractionthe resulting suspension was extracted three times with ethyl acetate (3×25 mL)
4. extractionThe combined ethyl acetate extract
5. washwas washed once with brine (~ 30 mL)
6. dry with materialwas then dried over magnesium sulfate
7. filtrationAfter filtration
8. customthe solvent was removed under reduced pressure
9. customto yield an oil which
10. customsuch in the next reaction

ORD record

ord-1d8f6010322943cc915641faa74f5139

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05656426