Hydrochloric Acid → Racemic (4aSR,7aSR)-7a-(5-Bromo-2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine

Participants

Reaction Conditions

Reaction Steps

5 N Aqueous hydrochloric acid (158 mL) is added to N-(7a-(5-bromo-2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide (16.35 g, 7.89 mmol) and the mixture is heated to 90° C. After 18 hours, the mixture is allowed to cool to ambient temperature and washed with dichloromethane. The organic layer is extracted once with 5 N aqueous hydrochloric acid. The pH of the aqueous layer is adjusted to basic with 50% aqueous sodium hydroxide and is extracted twice with 10% isopropyl alcohol:dichloromethane. The organic layer is concentrated under reduced pressure. The resulting residue is purified by radial chromatography eluting with 2% to 5% 7 N ammonia in methanol:dichloromethane to give the title compound (2.23 g, 47%). ES/MS m/e (79Br/81Br) 331, 333 (M+1).

Provenance & Evidence