Dichloromethane → tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 4-(tosyloxy)piperidine-1-carboxylate (5.50 g, 15.40 mmol, 1 eq) and DBU (5.70 g, 31.00 mmol, 2 eq) in DMF (100 mL) was heated at 150° C. overnight and cooled to room temperature. To this, 100 mL of CH2Cl2 was added, and the mixture was washed with brine (20 mL×3) and water (30 mL×2). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (10:1 (v/v) PE/EtOAc) to give the title compound as pale yellow oil (2.40 g, 85.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 184.1 (M+1).

Provenance & Evidence