Sodium Hydroxide → HCID 69083750, compound

Participants

Reaction Steps

A cooled (0° C.) solution of 1 M LHMDS in THF (1.25 ml; 1.25 mmol; 1.2 equiv.) in anh. THF (2 ml) was treated dropwise with a solution of 1-(4-(trifluoromethoxy)benzyl)piperidine-2,6-dione (300 mg; 1.04 mmol; 1.0 equiv.) in anh. THF (2 ml), and the resulting mixture was stirred at rt, under nitrogen, for 1 h. The obtained mixture was cooled to −78° C., and treated with a solution of diphenyl phosphorochloridate (343 mg; 1.25 mmol; 1.2 equiv.) in anh. THF (1 ml). Stirring was continued at −78° C. for 10 min., and at rt for 1.5 h. A solution of 10% aq. NaOH (25 ml) was added, and the obtained mixture was extracted with Et2O (3×). The mixed organic layers were dried over anh. K2CO3, filtered, and concentrated to dryness under reduced pressure affording 6-oxo-1-(4-(trifluoromethoxy)benzyl)-1,4,5,6-tetrahydropyridin-2-yl diphenyl phosphate as a yellow oil which was directly used for the next reaction. LC-MS (conditions E): tR=0.84 min.; [M+H]+: 520.19 g/mol.

Provenance & Evidence