Hydrochloric Acid → HCID 20081437, compound

Participants

Reaction Conditions

Reaction Steps

Potassium t-butoxide (5.3 g) was added with stirring and cooling to the product of Example 1 (7.5 g) in dry tetrahydrofuran (120 ml). The mixture was stirred for 41/2 hours at room temperature, and was then cooled to 5° C., when iodomethane (3.2 g) in dry tetrahydrofuran (10 ml) was added dropwise. Stirring was continued at room temperature for 24 hours, and the intermittently for 7 days. The solvent was run off under vacuum, and the residue was stirred with ice, water and ether while being acidified to pH=1 with hydrochloric acid. The ether solution was separated, the aqueous layer being extracted twice more with ether, and the combined ether extracts were washed with water (twice), dried over magnesium sulfate, and run down under vacuum to give the desired product (7.1 g) in am impure form. Purification by flash chromatography on silica gel, eluting with dichloromethane and ethyl acetate (9:1), followed by preparative HPLC gave 0.4 g of the pure desired product, mp 124°-127° C.

Provenance & Evidence