Triphenylphosphine → 5-(4-Methoxy-phenyl)-7-methyl-2-(3-piperidin-1-yl-propoxy)-5,6,7,8-tetrahydro-[1,7]naphthyridine

Participants

Reaction Steps

To a mixture of 5-(4-methoxy-phenyl)-7-methyl-5,6,7,8-tetrahydro-[1,7]naphthyridin-2-ol (0.10 g, 0.37 mmol) and PPh3 (0.097 g, 0.37 mmol) in THF (5 mL) was added a solution of di-tert-butyldiazodicarboxylate (0.085 g, 0.37 mmol) in THF (5 mL). After 30 min, a solution of 3-piperidin-1-yl-propan-1-ol (0.053 g, 0.37 mmol) in THF (5 mL) was added slowly. After 18 h, the mixture was concentrated, and the resulting solid was purified (SiO2; 0-8% 2 M NH3 in MeOH/DCM) to give the title compound (30 mg, 20%). MS (ESI): mass calcd. for C24H33N3O2, 395.26; m/z found, 396.6 [M+H]+. 1H NMR (CDCl3): 7.10-7.04 (m, 3H), 6.83 (d, J=8.6, 2H), 6.45 (d, J=8.4, 1H), 4.33-4.25 (m, 2H), 4.15-4.10 (m, 1H), 3.79 (s, 3H), 3.76-3.70 (m, 1H), 3.57-3.50 (m, 1H), 3.02-2.97 (m, 1H), 2.53-2.45 (m, 3H), 2.44 (s, 3H), 2.42-2.38 (m, 3H), 2.00-1.92 (m, 2H), 1.66-1.54 (m, 7H).

Provenance & Evidence