Sodium Hydroxide → 1-Benzyl-3-(1-tert-butoxycarbonylaminocyclobutyl)pyrrolidine

Participants

Reaction Steps

A 1.01 g (4.13 mmol) portion of 1-benzyl-4-(1-aminocyclobutyl)-2-pyrrolidone (fr. 1) was dissolved in 150.0 ml of tetrahydrofuran. Thereto was subsequently added 627 mg (16.52 mmol) of lithium aluminum hydride in small portions under ice cooling. After 12 hours of stirring with heating under reflux, the reaction solution was cooled in an ice bath and mixed with 627 μl of water in small portions, 627 μl of 15% sodium hydroxide aqueous solution and 627 μl of water in that order. After 30 minutes of stirring at room temperature, insoluble material was removed by filtration and the solvent was evaporated. To the thus obtained syrup were added 50.0 ml of acetonitrile and then 1.14 ml (4.96 mmol) of di-tert-butylcarbonate at room temperature, followed by overnight stirring. After evaporation of the solvent, the resulting residue was purified by a silica gel column chromatography (230-400 mesh silica gel 100 ml, 5% methanol-chloroform) to yield 212 mg (16%) of the title compound.

Provenance & Evidence