Triphenylphosphine → HCID 66974094, compound

Participants

Reaction Conditions

Reaction Steps

A solution consisting of 3-(2-hydroxy-ethyl)-azetidine-1-carboxylic acid tert-butyl ester (4.39 g, 21.8 mmol), 3-(4-chloro-phenoxy)-phenol (4.81 g, 21.8 mmol) and THF (40 mL) was cooled at 0° C., treated with polymer supported triphenyl phosphine (10.9 g, 32.7 mmol) then diisopropyl azodicarboxylate (6.62 g, 32.7 mmol) dropwise over 30 min. After stirring for 15 min at 0° C., the reaction mixture was allowed to warm to room temperature and stirred for 16 h. The reaction mixture was filtered, the filtrate evaporated, and the residue purified (FCC) to give the title compound as a clear oil (6.39 g, 73%). MS (ESI+): calcd. for C22H26ClNO4, 403.16. m/z found, 426.2 (M+Na)+. 1H NMR (d6-DMSO): 7.43 (d, J=9.0 Hz, 2H), 7.28 (t, J=8.2 Hz, 1H), 7.03 (d, J=9.0 Hz, 2H), 6.72 (dd, J=8.3, 1.5 Hz, 1H), 6.59-6.55 (m, 2H), 3.98-3.84 (m, 4H), 3.59-3.50 (m, 2H), 2.70-2.58 (m, 1H), 2.02-1.89 (m, 2H), 1.36 (s, 9H).

Provenance & Evidence