Borane;tetrahydrofuran → HCID 68685710, compound

Participants

Reaction Steps

4-cyclopropylmethanesulfonyl-1-(pyrrolidine-1-carbonyl)-cyclohexanecarbonitrile (246 mg; 0.0758 mmol) and borane-THF complex (1.0 M solution in THF; 10 ml; 10 mmol) were stirred at room temperature overnight. LC-MS indicated that the reaction had not gone to completion. The mixture was heated at reflux for 2 hours then allowed to cool to room temperature. The mixture was cooled in an icebath and quenched with MeOH (3 ml) then evaporated to dryness in vacuo. The residue was dissolved in MeOH (7 ml) and acidified with concentrated HCl. The mixture was stirred at room temperature for 18 hours. The mixture was poured on to a SCX cartridge. The cartridge was washed with several column lengths of MeOH followed by 2M ammonia in methanol solution to elute the amine. The desired product was obtained as a colourless oil upon evaporation of the appropriate fractions (44 mg). m/z=315 (M+H+).

Provenance & Evidence