benzyl ((1R)-1-{[methyl(1-phenylprop-2-en-1-yl)amino]carbonyl}but-3-en-1-yl)carbamate → benzyl [(3R,7R)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl ((1R)-1-{[methyl(1-phenylprop-2-en-1-yl)amino]carbonyl}but-3-en-1-yl)carbamate (3b) (1.01 g) dissolved in Toluene (100 mL) at 80° C. under N2 was added Grubbs catalyst (2nd generation) (113 mg) and the reaction mixture was stirred at 80° C. for 50 min., cooled to RT and concentrated in vacuo. The crude product was directly purified via flash chromatography (gradient—10%, 15%, 20% and 30% EtOAc/hexanes) to give the title compound (3c) (331 mg) and benzyl [(3R,7R)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate (3d) (453 mg) (combined yield of 83%).

Provenance & Evidence