Iodine → Benzyl 3-formylpiperidine-1-carboxylate

Participants

Reaction Steps

A 500-mL round-bottomed flask was charged a solution of benzyl 3-(hydroxymethyl)piperidine-1-carboxylate (8.94 g, 35.90 mmol, 1.00 equiv) in DCM (200 mL), NaHCO3 (9.05 g, 107.74 mmol, 3.00 equiv) in H2O (80 mL), I2 (18.24 g, 71.81 mmol, 2.00 equiv) and TEMPO (570 mg, 3.65 mmol, 0.10 equiv). The resulting mixture was stirred for 18 hours at room temperature. The reaction progress was monitored by TLC (DCM:MeOH=20:1). Upon completion, the reaction was then quenched by the addition of 10 mL of NaHSO3/H2O. The pH was adjusted to 8 with NaHCO3. The resulting solution was extracted with dichloromethane (3×50 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator to afford benzyl 3-formylpiperidine-1-carboxylate as brown oil (6.2 g, (70%).

Provenance & Evidence