Nitrogen → Ethyl 3-amino-6-(1,4-dioxaspiro[4.5]dec-8-yl)pyridine-2-carboxylate

Participants

Reaction Steps

10% Pd/C (345 mg, 0.0812 mmol) was added to a solution of ethyl 3-amino-6-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine-2-carboxylate (Compound 232F, 247 mg, 0.812 mmol) in EtOH (5.0 mL). The flask containing this mixture was subjected to 3 cycles of evacuation and N2 purging. After the 4th evacuation the flask was purged with H2 and allowed to stir for 24 hours. The reaction mixture was filtered through celite, the filter cake was washed with MeOH and DCM. The combined filtrate was concentrated to 228 mg of a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 1.30 (t, J=7.07 Hz, 3H), 1.59 (dd, J=12.51, 5.43 Hz, 2H), 1.63-1.70 (m, 2H), 1.70-1.79 (m, 4H), 2.59 (tt, J=11.15, 3.51 Hz, 1H), 3.87 (s, 4H), 4.28 (q, J=7.07 Hz, 2H), 6.50 (s, 2H), 7.17 (s, 2H). MS (ES+): m/z=306.91 (100) [M+1]. HPLC: tR=3.19 min (ZQ3, polar—5 min).

Provenance & Evidence