tert-Butanol → HCID 18426153, compound

Participants

Reaction Steps

A solution of 1-(4-chlorobenzyl)nipecotic acid (7.06 g, 27.8 mmol) in tBuOH (500 mL) was treated with Et3N (3.38 g) and activated 3 A molecular sieves (30 g). Diphenylphosphoryl azide (8.58 g) was added, and the reaction mixture was warmed at reflux for 18 h. The mixture was cooled and the solvent was reflux for 18 h. The mixture was cooled and the solvent was remove under vacuum. The residue was dissolved in EtOAc (500 mL), and the organic phase was washed with saturated aqueous NaHCO3 (2×100 mL) and brine (50 mL), dried (Na2SO4), and concentrated in vacuo. Chromatography (SiO2, 25% EtOAc-hexane) afforded 1-(4-chlorobenzyl)-3-{(tert-butoxycarbonyl)amino}piperidine (2.95 g, 32.6%) as a white crystalline solid: 1H NMR (CDCl3, 300 MHz) δ 1.4-1.75 (br, 4 H), 2.2-2.7 (br, 4 H), 3.5 (br, 2 H), 3.8 (br, 1 H), 7.3 (br, 4 H); The purity was determined by RPLC/MS (>99%); ESI/MS m/e 269.2 (M++H-56, C17H26ClN2O2).

Provenance & Evidence