Acetonitrile → HCID 90406318, compound

Participants

Reaction Steps

CH3CN (0.25 mL, 4.79 mmol) was added to a cold (−78° C.) solution of t-BuO−K+ in THF (1M, 5.0 mL, 5.0 mmol) under Ar and the reaction mixture was stirred for 5 mins. Solution of tert-butyl 4-((3-(methoxycarbonyl)phenoxy)methyl)piperidine-1-carboxylate (1.01 g, 2.86 mmol) in anhydrous THF (7 mL) was added to the reaction mixture and the resulting mixture was stirred at −78° C. for 10 min, then warmed to room temperature over 30 mins. The reaction mixture was quenched with 5% aqueous NaHSO4 and extracted twice with tert-butyl methyl ether. Combined organic layers were washed with brine and concentrated under reduced pressure. Purification by flash chromatography (20%-80% EtOAc-hexanes gradient) gave tert-butyl 4-((3-(2-cyanoacetyl)phenoxy)methyl)piperidine-1-carboxylate as a white solid. Yield (0.55 g, 54%); 1H NMR (400 MHz, DMSO-d6) δ 7.39-7.51 (m, 3H), 7.23-7.28 (m, 1H), 4.73 (s, 2H), 3.84-4.00 (m, 2H), 3.90 (d, J=6.26 Hz, 2H), 2.60-2.80 (m, 2H), 1.86-1.97 (m, 1H), 1.70-1.78 (m, 2H), 1.38 (s, 9H), 1.08-1.23 (m, 2H).

Provenance & Evidence