Water → N-[2-(3,4-difluorophenyl)-4-oxobutyl]-N-methyl-5,6,7,8-tetrahydro-1-naphthamide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a stirred cooled (−78° C.) solution of oxalyl chloride (0.546 mL, 6.26 mmol) in DCM (2.55 mL) was added DMSO (0.888 mL, 12.52 mmol) in DCM (3.94). The solution was stirred at −78° C. for 5 min and a solution of N-[2-(3,4-difluorophenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydro-1-naphthamide (1.17 g, 3.13 mmol) in DCM (6.3 mL) and DMSO (3.32 mL) was added dropwise. The solution was stirred at −78° C. for 15 min and triethylamine (2.52 mL, 18.1 mmol) was added. Stirring was continued at −78° C. for 30 min and then at room temperature for 2 h. Additional H2O and DCM (25 mL) were added, the layers separated, and the organic layer was dried (MgSO4), filtered, and concentrated in vacuo. Purification by chromatography (silica gel; Et2O) provided the title compound (1.10 g, 95%) as a brown gum. MS m/z 372 (M+H).

Herkunft & Nachweise