HCID 21345251, compound → HCID 21345252, compound

Participants

Reaction Steps

6-methoxy-3-(1-Cbz-2-(R)-azetidinylmethoxy)pyridine from Example 119c (300 mg, 0.91 mmol) was combined with 10% Pd/C (50 mg) in 30 mL of EtOH, and the mixture was stirred under an H2 atmosphere for 16 hours. The mixture was filtered and concentrated. The crude free base was converted to the salt by treatment with p toluenesulfonic acid in ethyl acetate. The mixture was concentrated, the residue was triturated with ether, and the product was recrystalized from ethyl acetate/ether to give 167 mg (33.9%) of the title compound: mp 139-142° C.; 1H NMR (D2O 300 MHz) δ2.39 (s, 6H), 2.60-2.70 (m, 2H), 2.98 (s, 3H), 4.04-4.15 (m, 2H), 4.36 (d, J=4.5, 2H), 4.95 (m, 1H), 7.08 (d, J=9.0, 1H), 7.36 (d, J=8.0, 4H), 7.68 (d, J=8.0, 4H), 7.75 (dd, J=3.5, 9.5, 1H), 7.91 (d, J=3.0, 1H); MS (DCI/NH3) m/e 195 (M+H)+. Anal. calcd. for C10H14N2O2.2C7H8O3S: C, 53.52; H, 5.61; N, 5.20. Found: C, 53.24; H, 5.68; N, 5.07. [α]D +3.55(c 1, MeOH).

Provenance & Evidence