Hydrochloric Acid → 3-(1-Aminoethyl)-1-(benzyloxycarbonyl)piperidine

Participants

Reaction Steps

To a solution of 3-(1-azidoethyl)-1-(benzyloxycarbonyl)piperidine (1.95 g, 6.76 mmol) in THF (30.6 mL) was added Ph3P (2.66 g, 10.14 mmol) followed by water (3.4 mL). The mixture was placed in an oil bath at 50° C. for 2.5 h. The reaction mixture was cooled and carefully poured into an Erlenmeyer flask containing 1N HCl. The layers were separated, and the aqueous layer was washed once with EtOAc and the organic layer was discarded. The aqueous layer was then neutralized with saturated aqueous NaHCO3 carefully and was extracted with EtOAc (3×30 mL) and the organic extracts discarded. The aqueous layer was made strongly basic (>pH 12) with SN NaOH, then it was extracted with EtOAc (4×50 mL). The combined organic extracts were washed with brine and dried over Na2SO4. The title compound (950 mg) was used in the next step without purification. Partial 1H NMR (500 MHz, CDCl3): δ 7.3 (m, 5H); 5.12 (s, 2H); 4.1 (brm, 2H); 1.25 (br s, 3H).

Provenance & Evidence