Tert-butyl 1-(allyl(phenyl)amino)-3,3-dimethyl-1-oxopent-4-en-2-ylcarbamate → (Z)-tert-butyl 4,4-dimethyl-2-oxo-1-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added tert-butyl 1-(allyl(phenyl)amino)-3,3-dimethyl-1-oxopent-4-en-2-ylcarbamate (60 mg, 0.17 mmol) and 1,2-dichloroethane (2 mL). The reaction was charged with argon and brought to 60° C. Then, the Grubbs II catalyst (21 mg, 0.025 mmol) was added and the reaction was stirred at 60° C. for 4 hr and then at rt overnight. The reaction was concentrated and the residue was purified by RP prep-HPLC (Method A) to give (Z)-tert-butyl 4,4-dimethyl-2-oxo-1-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate (15 mg, 0.045 mmol, 27% yield) as a clear oil. Anal. Calcd. for C19H26N2O3 m/z 330.2. found: 331.2 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 7.38 (t, J=7.69 Hz, 2H), 7.30-7.25 (m, 1H), 7.21 (d, J=7.03 Hz, 2H), 5.82-5.71 (m, 2H), 5.71-5.64 (m, 1H), 5.10 (d, J=8.35 Hz, 1H), 4.82 (d, J=17.58 Hz, 1H), 3.76 (dd, J=17.58, 7.91 Hz, 1H), 1.50-1.44 (m, 9H), 1.20-1.16 (m, 3H), 0.99 (s, 3H).

Provenance & Evidence