Dichloromethane → Ammonia dichloromethane

Participants

Reaction Steps

A suspension of tert-butyl 4-hydroxy-1-piperidine carboxylate (497 mg), 4-phenylphenol (300 mg), and polymer-supported triphenylphosphine (1.2 g) in DCM (10 mL) was treated with di-tert-butyl azodicarboxylate (608 mg). The resulting mixture was shaken for 16 h, and filtered through a pad of celite. The pad was washed with DCM (3×5 mL) and the combined filtrates were evaporated. The residue was dissolved in dioxane (5 mL) and treated with hydrogen chloride (5 mL of a 4 N solution in dioxane). After 16 h, solvent was removed and the residue was treated with 10% aqueous sodium hydroxide (20 mL). The resulting mixture was extracted with DCM (2×500 mL), and the combined organic phases were dried (magnesium sulfate) and evaporated. Chromatography of the residue (1-6% 2M methanolic ammonia/DCM) gave the title compound as a white solid (107 mg). 1H NMR (400 MHz, CDCl3): 7.56-7.49 (m, 4H), 7.42-7.39 (m, 2H), 7.31-7.27 (m, 1H), 6.99-6.96 (m, 2H), 4.43-4.37 (m, 1H), 3.18-3.13 (m, 3H), 2.77-2.70 (m, 2H), 2.07-2.01 (m, 2H), 1.73-1.64 (m, 2H).

Provenance & Evidence