Cyanomethylenetributylphosphorane → 1-Boc-3-[5-bromo-2-(3-chloro-benzyloxy)-phenoxymethyl]-azetidin-3-ol

Participants

Reaction Conditions

Reaction Steps

The mixture of the title compound of Example 215 Step B (2.3 mmol), 5-bromo-2-(3-chloro-benzyloxy)-phenol (1.3 mmol), and cyanomethylenetri-n-butylphosphorane (2 mmol) in toluene (5 mL) was heated at 150° C. in a microwave reactor for 1 h. The mixture was cooled to rt and purified by PTLC providing the title compound (580 mg). MS (ESI): mass calcd. for C22H25BrClNO5, 497.1; m/z found, 504.2 [M-OH+Na]+. 1H NMR (CDCl3): 7.52-7.23 (m, 4H), 6.99-6.68 (m, 3H), 5.70-5.10 (br S, 1H), 5.04 (s, 2H), 4.99-4.97 (m, 2H), 4.50-4.46 (m, 4H), 1.45 (s, 9H).

Provenance & Evidence