2-Methyltetrahydrofuran → HCID 178480322, compound

Participants

Reaction Steps

A solution of 2-({5-[(2S)-1-methylpyrrolidin-2-yl]pyridin-3-yl}oxy)ethanamine (preparation 12) (55 mg, 0.25 mmol) in 2-methyltetrahydrofuran (2 ml) was treated, with stirring, with trans-4-tert-butoxycarbonyl-cyclohexane carboxylic acid (91 mg, 0.373 mmol) followed by T3P (317 μl, 0.498 mmol) and the Et3N(118 μl, 0.91 mmol). After stirring for 3 hours, the solution was treated with T3P (69 μL, 0.498 mmole). 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 methanol 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). This material was then dissolved in DCM and treated with PS-Isocyanate resin for 3 hours then filtered and evaporated in-vacuo to give the title compound as a pale yellow gum (35 mg, 35%);

Provenance & Evidence