4-(N-Boc-amino)piperidine → HCID 68778000, compound

Participants

Reaction Steps

A mixture of Example 360 (150 mg, 0.27 mmol), 4-(tert-butoxycarbonylamino)-piperidine (105 mg, 0.52 mmol), potassium tert-butoxide (45 mg, 0.37 mmol) and acetato(2′-di-tert-butylphosphino-1,1′-biphenyl-2-yl)palladium(II) (20 mg, 0.043 mmol) in 1,4-dioxane (6.0 mL) was heated in a sealed tube at 100° C., under microwave irradiation, for 30 minutes. The solvent was removed in vacuo and the residue was purified by column chromatography (SiO2, 0-100% EtOAc/heptane). A sample of the obtained solid (43 mg) was taken up in DCM (8.0 mL), treated with trifluoroacetic acid (2.0 mL) and stirred at room temperature for 4 h. The reaction mixture was partitioned between DCM (20 mL) and saturated aqueous sodium hydrogencarbonate solution (20 mL). The organic phase was dried (magnesium sulfate), the solvent was removed in vacuo and the residue was purified by column chromatography (0-20% MeOH/DCM, 1% NH4OH) to give the title compound (23 mg, 33%) as a clear glass. δH (CD3OD) 8.68 (1H, d, J 5.1 Hz), 7.91 (1H, s), 7.64-7.59 (1H, m), 7.46-7.33 (3H, m), 7.15-7.06 (1H, m), 3.87-3.77 (2H, m), 3.72-3.64 (4H, m), 3.10-3.00 (4H, m), 2.92-2.75 (3H, m), 2.63 (2H, s), 2.46 (2H, s), 2.01-1.90 (2H, m), 1.63-1.47 (2H, m), 1.04 (6H, s). LCMS (ES+) 517.3 (M+H)+.

Provenance & Evidence