tert-butyl (S)-1-oxo-1-((R)-2-vinylpiperidin-1-yl)pent-4-en-2-ylcarbamate → tert-butyl (7S,10aR,Z)-6-oxo-1,2,3,4,6,7,8,10a-octahydropyrido[1,2-a]azepin-7-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl (S)-1-oxo-1-((R)-2-vinylpiperidin-1-yl)pent-4-en-2-ylcarbamate (1.00 gm, 3.24 mmol) in DCE (350 mL) was purged with argon for 10 min. Grubbs II catalyst (0.124 gm, 0.146 mmol) was added and the reaction mixture was heated at 60° C. under argon for 18 hr. The reaction mixture was concentrated. The crude product was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give tert-butyl (7S,10aR,Z)-6-oxo-1,2,3,4,6,7,8,10a-octahydropyrido[1,2-a]azepin-7-ylcarbamate (653 mg, 2.33 mmol, 71.8% yield) as a solid. Anal. Calcd. for C15H24N2O3 m/z 280.3. found: 281.0 (M+H)+.

Provenance & Evidence