HCID 59371635, compound → HCID 59371305, compound

Participants

Reaction Steps

In a 100 mL round-bottom flask with magnetic stirrer and H2 balloon, 2-[3-[5-[[1-(benzyloxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]phenyl]ethanol (240 mg, 574 μmol) in MeOH (10 mL) was stirred with 10% Pd/C (50 mg; Alfa Aesar #38305, water content 50%) at room temperature for 130 min. H2 was replaced with Ar, and the catalyst was filtered off over a cotton plug and rinsed with MeOH (2 mL). The solution was evaporated and dried (30° C., oil pump vacuum) to yield the free base as a colorless film. [α]D−1.0, [α]546−1.4 (c 7.35 g/L, MeOH). 1H NMR (CDCl3, TMS, 400 MHz) δ 8.41 (d, 1H, J=1.8 Hz), 8.28 (d, 1H, J=2.8 Hz), 7.45-7.40 (m, 3H), 7.39 (dd, 1H, J=1.8, 2.8 Hz), 7.28 (dt, 1H, J=6.4 Hz (d), 2.1 Hz (t)), 4.31 (m, 1H), 4.12, 4.08 (ABq, 2H, J=9.4 Hz, low-field part d with J=6.2 Hz, high-field part d with J=4.8 Hz), 3.92 (t, 2H, J=6.6 Hz), 3.72 (q, 1H, J=7.9 Hz), 3.48 (m, 1H), 2.95 (t, 2H, J=6.6 Hz), 2.41, 2.29 (ABq, 2H, J=11.0 Hz, low-field part m, high-field part q with J=8.2 Hz), 2.08 (br, NH, OH, and H2O). MS (EI) m/z 284 (M+, 1.9%), 254 (2.2%), 229 (36%), 228 (56%), 199 (10%), 56 (100%).

Provenance & Evidence