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

Participants

Reaction Steps

A solution of 1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinecarbaldehyde (1.1 g, 4.93 mmol) in THF (25 mL) at −10° C. was treated dropwise with methylmagnesium bromide (3M in Et2O, 3.94 mL, 11.8 mmol). The mixture was stirred at −10° C. to −5° C. over a 2 h period. The reaction was carefully quenched by the addition of saturated aqueous NH4Cl and the aqueous was extracted with ether (6 mL×2). The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated. The crude material was purified by chromatography on a silica gel column eluted with 0 to 70% EtOAc/hexanes to give 0.39 g (33%) of (±)-1-{1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethanol as a light yellow oil.

Provenance & Evidence