Piperidine → Tert-butyl 3-(piperidin-1-ylmethyl)azetidine-1-carboxylate

Participants

Reaction Steps

To a suspension of 3-methanesulfonyloxymethylazetidine-1-carboxylic acid tert-butyl ester (0.36 g, 1.40 mmol) in toluene (2 mL) was added piperidine (0.7 mL, 7.00 mmol) and the resultant mixture was heated to 110° C. in a sealed tube for 18 h. The solution was concentrated in vacuo, the crude residue dissolved in DCM and washed with 0.5 N KOH (aq.) (1×) and brine (1×). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The resultant oil was purified by chromatography on silica gel with MeOH:DCM (1:19, v/v) as eluent to afford 3-piperidin-1-ylmethylazetidine-1-carboxylic acid tert-butyl ester (180 mg, 0.70 mmol, 50%) as an oil.

Provenance & Evidence