Ethyl 4-piperidinecarboxylate → Ethyl 1-(4-(tert-butoxycarbonyl)phenyl)piperidine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

1\. To a microwave tube was added tert-butyl 4-bromobenzoate (1.328 g, 5.16 mmol), ethyl piperidine-4-carboxylate (1.000 g, 5.16 mmol), Cs2CO3 (5.05 g, 15.49 mmol), Pd2dba3 (0.473 g, 0.52 mmol), and BINAP (0.643 g, 1.03 mmol). The mixture was dissolved in [Solvents] and sealed. The tube was de-gassed and inflated with N2. 2\. The reaction was heated at 110°C in oil-bath overnight. LCMS showed reaction complete. The reaction mixture was filter through celite pad and the solution was loaded to column for a ISCO purification (30% EtOAc in Hex). The purification is difficult with multiple by-products. Several ISCO purification was carried out and fractions were combined with other batches. Yield was poor.

Provenance & Evidence