Acetonitrile dry ice → HCID 117635647, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred yellow solution of ethyl 5-(4-(allyloxy)-4-methylpiperidin-1-yl)-6-(2-methoxy-2-oxoacetyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylate (0.86 g, 1.94 mmol, 1 equiv) in toluene (19 mL) was added (R)-1-methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole/toluene (0.54 g, 1.94 mmol, 1 equiv). The reaction was cooled to −40° C. (acetonitrile/dry ice bath) and a solution of 50% catechoborane in toluene (0.93 mL, 3.88 mmol, 2 equiv) was added over 10 min. The reaction mixture was stirred at −15° C. for 2 h. Upon completion, the reaction was diluted with EtOAc (30 mL) and sat. NaHCO3 (10 mL). The mixture was stirred vigorously for 30 min. The organic phase was washed with saturated aqueous NaHCO3 (2×5 mL), dried (Na2SO4), and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-10% MeOH/DCM) to afford desired product (0.86 g, 100%) as an off-white solid. LCMS (ESI, M+1): 446.25.

Provenance & Evidence