Triethylamine → (+/-)-1-{1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

A solution of (±)-1-{1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethanol (0.39 g) in CH2CH2 (35 mL) at 0° C. was treated with methanesulfonyl chloride (0.26 mL, 3.26 mmol) and Et3N (0.69 mL, 4.89 mmol) and stirred at 0° C. for 1 h then room temperature for 15 h. The mixture was diluted with CH2CH2 (80 mL), washed with 1M NaH2PO4 (50 mL×2) and brine (35 mL), and dried over Na2SO4 and concentrated to afford crude (±)-1-{1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethyl methanesulfonate (0.53 g, 100%) as a light brown oil. The crude product was used without further purification. 1H NMR (400 MHz, CDCl3): δ 4.75-4.65 (m, 1H), 4.30-4.15 (m, 2H), 3.10-2.95 (m, 5H), 2.89 (septet, 1H, J=7.0 Hz), 1.95-1.70 (m, 3H), 1.55-1.35 (m, 5H), 1.28 (d, 6H, J=6.9 Hz).

Provenance & Evidence