Methyl iodide → HCID 89922465, compound

Participants

Reaction Steps

To a solution of (+/−)-benzyl 9-oxohexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate (160 mg, 0.553 mmol) in THF (5 mL) at 0° C. was added sodium hydride (24.33 mg, 0.608 mmol). The ice bath was removed and stirred for 10 min; saw bubbling but some NaH solid still remained. Then iodomethane (0.038 mL, 0.608 mmol) was added and after stirring for 10 min at room temperature, most NaIl solid was dissolved. After another 30 min, LC-MS indicated completion. It was quenched with water and diluted with EtOAc. After separating the layers, the aqueous layer was further extracted with EtOAc. The combined organic extracts were washed with water, brine, dried over MgSO4, filtered and concentrated. Purification via flash chromatography (0-5% MeOH in DCM, 12 g) gave (+/−)-benzyl 8-methyl-9-oxohexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate (120 mg) as a light yellow oil.

Provenance & Evidence