tert-Butanol → HCID 18426153, compound

Participants

Reaction Steps

Triethylamine (3.38 g) and activated 3 Å molecular sieve (30 g) were added to a tBuOH (500 mL) solution of 1-(4-chlorobenzyl)nipecotic acid (7.06 g, 27.8 mmol). Diphenylphosphoryl azide (8.58 g) was added, and the resulting reaction mixture was stirred under reflux for 18 hour and cooled. The solvent was removed under reduced pressure. The obtained residue was then dissolved in ethyl acetate (500 mL), and the organic layer was washed with a saturated aqueous solution of NaHCO3 (100 mL×2) and brine (50 mL), then dried (over Na2SO4) and concentrated under reduced pressure. The obtained crude product was purified by chromatography (SiO2, 25% ethyl acetate-hexane) to provide 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, 4H), 2.2-2.7 (br, 4H), 3.5 (br, 2H), 3.8 (br, 4H), 7.3 (br, 4H). The purity was determined by RPLC/MS (>99%). ESI/MS m/e 269.2 (M++H-56, C17H26ClN2O2).

Provenance & Evidence