Pyridine → HCID 12017802, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (R)-2-amino-4-methyl-pentanoic acid benzyl ester (Bachem, 14.1 g, 63.6 mmol) and pyridine (25 mL, 0.31 mmol) in 400 mL of CH2Cl2 was cooled to 0° C. and treated rapidly with phosgene (40 mL of a 1.9 M solution in toluene) in one portion. The resulting solution was stirred at 0° C. for 2 hours and then treated with hexamethylenimine (9.3 mL, 82.7 mmol) in CHCl3 (25 mL). The resulting solution was warmed to room temperature and concentrated. The residue was dissolved in ether and washed with aqueous 1N HCl solution. The organic phase was dried (MgSO4), filtered, and concentrated. The crude residue was purified by chromatography (silica gel, 2:1 heptane/ethyl acetate) to give the title compound as a yellow solid (4.96 g, 68%), mp=88-89° C.

Provenance & Evidence