Methyl iodide → HCID 22875671, compound

Participants

Reaction Steps

To a solution of 20 mg (0.06 mmol) 20-hydroxy-4,7β,20-trimethyl-5α-4-azapregnan-3-one (from Example 2) in 4 ml dry dimethylformamide at 0° C. was added methyl iodide (10 eq, 0.6 mmol) and sodium hydride (5 eq, 0.3 mmol) were added and the reaction was stirred at RT for 48 hours. Aqueous ammonium chloride was added and the reaction mixture was poured onto 100 ml water and extracted with three 25 ml portions of ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulfate, and evaporated. The product was purified via HPLC on a 19×300 mm 8 micron silica column using 5% isopropanol/hexane eluent at 20 ml/min to yield 15 mg (0.04 mmol, 67% yield) of the title compound.

Provenance & Evidence