N-vinyl-2-pyrrolidone → HCID 11776313, compound

Participants

Reaction Steps

To a solution of 504.1 mg (3.93 mmol) of pyrrolidin-1-yl-acetaldehyde oxime prepared in Example 3 in 5 mL of tetrahydrofuran, 578 mg (1.1 equivalent) of N-chlorosuccinimide (NCS) was added, and then the mixture was reacted at 50° C. for 1 hour. To this solution, a solution of 630 μL (1.5 equivalent) of N-vinyl pyrrolidin-2-one in 30 mL of toluene was added, and 630 μL (1.1 equivalent) of triethylamine was added. After completion of the reaction, chloroform and a saturated aqueous solution of sodium carbonate were added, the mixture was extracted with chloroform three times, washed with a saturated aqueous solution of sodium carbonate twice following water once, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The dried compound was purified by separation with silica gel column chromatography using chloroform/methanol (gradient of 30:1 to 20:1) as eluent to obtain 102.2 mg (11% yield) of 1-[3-(pyrrolidin-1-yl-methyl)-4,5-dihydro-isoxazol-5-yl]-pyrrolidin-2-one. Subsequently, 1:1 acid addition salt with oxalic acid was obtained from the diethyl ether solution.

Provenance & Evidence