Benzyl 4-(2-(dimethylamino)-2-oxoethoxy)piperidine-1-carboxylate → Benzyl 4-(2-(dimethylamino)ethoxy)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Benzyl 4-(2-(dimethylamino)-2-oxoethoxy)piperidine-1-carboxylate (81) (4.5 g, 14.05 mmol) was dissolved in dry THF (50 mL), to this was added borane-methyl sulfide complex (10.53 mL, 21.07 mmol) and the reaction was stirred at 40° C. for 3 hours then at ambient temperature overnight. The gummy mixture was evaporated and was quenched with 2.0 N Na2CO3 (50 mL), extracted with EtOAc (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford the desired material as a colourless liquid (4.00 g, 93% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.60-1.51 (2H, m), 1.88-1.78 (2H, m), 2.65 (6H, s), 2.97 (2H, t), 3.29-3.22 (2H, m), 3.54-3.48 (1H, m), 3.79-3.73 (2H, m), 3.85 (2H, t), 5.12 (2H, s), 7.36-7.28 (5H, m).

Provenance & Evidence