HCID 59371468, compound → HCID 59371286, compound

Participants

Reaction Steps

In a 100 mL round-bottom flask with magnetic stirrer and H2 balloon, tert-butyl [3-[5-[[1-(benzyloxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]benzyl]carbamate (91.2 mg, 181 μmol) in MeOH (3 mL) was stirred with 10% Pd/C (19 mg; Alfa Aesar #38305, water content 50%) at room temperature for 2.5 h. H2 was replaced with Ar, and the catalyst was filtered off over a cotton plug and rinsed with MeOH (1.5 mL). The solution was evaporated and dried (35° C., oil pump vacuum) to yield the free azetidine (67.3 mg, 101%, must contain a trace of solvent) as a colorless film. [α]D0, [α]5460 (c 6.4 g/L, MeOH). 1H NMR (CDCl3, 500 MHz) δ 8.46 (br s, 1H), 8.32 (br s, 1H, J=2.8 Hz), 7.51-7.34 (m, 5H), 4.98 (br, 1H), 4.42 (narrow m, 1H), 4.34 (m, 1H), 4.18-4.08 (m, 2H), 3.75 (q, 1H, J=7.9 Hz), 3.50 (m, 1H), 2.44 (m, 1H), 2.33 (m, 1H), 1.89 (br, 2H), 1.49 (s, 9H). MS (EI) m/z 369 (M+, 0.1%), 314 (15%), 313 (21%), 257 (23%), 214 (24%), 213 (11%), 70 (11%), 56 (100%).

Provenance & Evidence