2-Methyltetrahydrofuran → HCID 178480320, compound

Participants

Reaction Steps

A solution of 3-{5-[(2S)-1-methylpyrrolidin-2-yl]pyridin-3-yl}propan-1-amine (preparation 4) (100 mg, 0.45 mmol) in 2-methyltetrahydrofuran (2 ml) was treated, with stirring, with trans-4-tert-butoxycarbonyl-cyclohexane carboxylic acid (132 mg, 0.502 mmol) followed by T3P (580 μl, 0.91 mmol) and then Et3N (118 μl, 0.91 mmol). After stirring for 3 hours, the solution was treated with T3P (240 μL, 0.38 mmol). After stirring for 18 hours the solution was concentrated in vacuo and the residue was taken up in MeOH and applied to an SCX-2 cartridge which was eluted with MeOH followed by ammonia in MeOH (˜2M). Product containing fractions were concentrated in vacuo and the residue purified by column chromatography on silica gel eluting with EtOAc:MeOH:NH3 (gradient from 1:0:0 to 90:10:1) to give the title compound as a gum (130 mg, 64%).

Provenance & Evidence