Sodium hydride → 1,1-Dimethylethyl 4-(3-methyl-1,2,4-oxadiazol-5-yl)-1-piperidinecarboxylate

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Reaction Steps

A solution 1.30 g (17.49 mmol) of acetamide oxime in 55 ml THF was treated with 0.76 g (17.49 mmol) of NaH (55% in oil) and the corresponding suspension stirred for 45 min at RT. 3.00 g (11.66 mmol) of ethyl 1-tert-butoxycarbonylpiperidine-4-carboxylate dissolved in 15 ml of THF was added and heated at 65° C. for 2 h. The solution was cooled to RT, poured on aqueous saturated NH4Cl solution and extracted with Et2O (3×). The organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% KHSO4, dried (Na2SO4) and evaporated to give 2.19 g (70%) of the title compound as orange liquid. MS: 268.2 (MH+).

Provenance & Evidence