Sodium Hydroxide → HCID 13491118, compound

Participants

Reaction Steps

A stirred mixture of about 4.1 g of 6,6-dimethoxy-5-(p-methyl-phenyl)-3-azabicyclo[3.2.0]heptane and about 50 ml of approximately 10% hydrochloric acid was heated under reflux for about 30 minutes. The solution was made basic with 5N sodium hydroxide and then was extracted with dichloromethane. The extract was dried over sodium sulfate, filtered, and evaporated under reduced pressure to give about 2.8 g of 5-(p-methylphenyl)-3-azabicyclo[3.2.0]heptane-6-one, b.p. 125°-130° C. (0.2 mm), as a yellow liquid. The fumarate salt had m.p. 130°-133° C. A mixture of about 3.8 g of the ketone, about 5 ml of 1,2-ethanedithiol and about 5 ml of freshly distilled boron trifluoride etherate in about 40 ml of acetic acid was stirred at room temperature for approximately 4 days, and then was evaporated under reduced pressure to give a tarry residue. This residue was slurried with ether and about 10% hydrochloric acid, and then the aqueous phase was made basic with approximately 5N sodium hydroxide and extracted with dichloromethane. The extract was dried over sodium sulfate and evaporated to give about 4.1 g of a solid. Recrystallization from acetonitrile gave 5-(p-methylphenyl)-3-methyl-spiro[3-azabicyclo[3.2.0]heptane-6,2'-[1,3]-dithiolane] as a tan solid, m.p. 81°-86° C.

Provenance & Evidence