tert-butyl 4-(phenoxymethyl)piperidine-1-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: tert-Butyl 4-(hydroxymethyl)piperidine-1-carboxylate (0.300 g, 1.393 mmol), phenol (0.122 mL, 1.393 mmol), triphenylphosphine (0.440 g, 1.672 mmol) and N-{[(tert-butoxy)carbonyl]imino}(tert-butoxy)formamide (0.390 g, 1.672 mmol) were combined in THF (4 mL) and stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure and purified by FCC (EtOAc: heptane, 1:1) to afford a white solid. This was further purified by trituration with diethyl ether to afford the title compound (0.289 g, 71%). Method B HPLC-MS: MH+ requires m/z=292 Found: m/z=235 (MH+-tBu), Rt=2.44 min (71%). The reaction mixture was concentrated under reduced pressure purified by FCC (EtOAc: heptane, 1:1) to afford a white solid This was further purified by trituration with diethyl ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: tert-Butyl 4-(hydroxymethyl)piperidine-1-carboxylate (0.300 g, 1.393 mmol), phenol (0.122 mL, 1.393 mmol), triphenylphosphine (0.440 g, 1.672 mmol) and N-{[(tert-butoxy)carbonyl]imino}(tert-butoxy)formamide (0.390 g, 1.672 mmol) were combined in THF (4 mL) and stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure and purified by FCC (EtOAc: heptane, 1:1) to afford a white solid. This was further purified by trituration with diethyl ether to afford the title compound (0.289 g, 71%). Method B HPLC-MS: MH+ requires m/z=292 Found: m/z=235 (MH+-tBu), Rt=2.44 min (71%). The reaction mixture was concentrated under reduced pressure purified by FCC (EtOAc: heptane, 1:1) to afford a white solid This was further purified by trituration with diethyl ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: tert-Butyl 4-(hydroxymethyl)piperidine-1-carboxylate (0.300 g, 1.393 mmol), phenol (0.122 mL, 1.393 mmol), triphenylphosphine (0.440 g, 1.672 mmol) and N-{[(tert-butoxy)carbonyl]imino}(tert-butoxy)formamide (0.390 g, 1.672 mmol) were combined in THF (4 mL) and stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure and purified by FCC (EtOAc: heptane, 1:1) to afford a white solid. This was further purified by trituration with diethyl ether to afford the title compound (0.289 g, 71%). Method B HPLC-MS: MH+ requires m/z=292 Found: m/z=235 (MH+-tBu), Rt=2.44 min (71%). The reaction mixture was concentrated under reduced pressure purified by FCC (EtOAc: heptane, 1:1) to afford a white solid This was further purified by trituration with diethyl ether