Methyl chloroformate → HCID 22961826, compound

Participants

Reaction Steps

5-Aminomethyl-3-(1-BOC-2-(S)-azetidinylmethoxy)-6-chloropyridine (0.23 g, 0.70 mmol) from Example 92b in CH2Cl2 (5 mL) at 0° C. was treated with NEt3 (0.2 mL, 1.40 mmol) and methyl chloroformate (0.061 mL, 0.80 mmol). The mixture was allowed to warm to room temperature and stir for 1 h. The volatile components were evaporated and the residue was chromatographed (silica gel; MeOH/CH2Cl2, 1:19) to afford the title compound as a yellow oil (0.22 g, 82%). 1H NMR (CDCl3, 300 MHz) δ 1.42 (s, 9H), 2.28-2.35 (m, 2H), 3.71 (s, 3H), 3.89 (t, J=7.5 Hz, 2H), 4.10 (dd, J=3.0, 10.0 Hz, 1H), 4.36 (m, 1H), 4.40 (d, J=6.5 Hz, 2H), 4.54 (m, 1H), 7.35 (d, J=3.5 Hz, 1H), 8.01 (d, J=3.0 Hz, 1H); MS (CI/NH3) m/z 386 (M+H)+.

Provenance & Evidence