Phosgene → tert-Butyl N-allyl-N-{[allyl(cyclopropylmethyl)amino]carbonyl}glycinate

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Reaction Conditions

Reaction Steps

To an ice-cooled solution of tert-butyl N-allylglycinate (Senokuchi et al. J. Med. Chem. 1995, 38, 2521) (308 mg, 1.80 mmol) in anhydrous THF (10 mL) was added phosgene (0.89 mL of a 20% solution in toluene, 1.80 mmol), then triethylamine (0.25 mL, 1.80 mmol). The resulting solution was stirred at 0° C. for 1 h, then N-(cyclopropylmethyl)prop-2-en-1-amine from Step A (200 mg, 1.80 mmol) was added, followed by triethylamine (0.75 mL, 5.40 mmol). The reaction mixture was allowed to warm to ambient temperature and stirring was continued for 18 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and water. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give a crude product, which was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 90:10 to provide the title compound. MS: m/z=309 (M+1).

Provenance & Evidence