1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 57827512, compound

Participants

Reaction Conditions

Reaction Steps

N-((4aS,5S,7aS)-5-(fluoromethyl)-7a-(2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide (70.56 g, 181.65 mmol) was dissolved in methanol (420 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (55.73 mL, 372.69) was added, and the solution was heated to reflux (heating block temperature 80° C.) for 5 h. The reaction mixture was concentrated under reduced pressure, and the residue purified by silica gel column chromatography (10% to 50% EtOAc in hexanes) to afford the title compound (46.05 g, 89%). 1H NMR (400 MHz, CDCl3) δ ppm 2.79 (dd, J=13.39, 4.04 Hz, 1H) 2.98-3.05 (m, 1H) 3.12 (dd, J=13.39, 3.54 Hz, 1H) 3.87 (dd, J=8.46, 2.65 Hz, 1H) 4.46 (br. s., 2H) 4.48-4.67 (m, 4H) 7.06 (ddd, J=12.57, 8.15, 1.26 Hz, 1H) 7.15 (td, J=7.58, 1.26 Hz, 1H) 7.24-7.31 (m, 1H) 7.44 (td, J=8.08, 2.02 Hz, 1H).

Provenance & Evidence