4'-Hydroxyacetophenone → 4-(4-Acetylphenoxy)piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

A solution of 1-(4-hydroxyphenyl)ethanone (1.48 g, 10.9 mmol) and tributylphosphine (3.0 g, 14.9 mmol) in toluene (20 ml) was treated dropwise at 0° C. with a solution of 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (2 g, 9.94 mmol) and 1,1′-(azodicarbonyl)dipiperidine (2.75 g, 10.9 mmol) in toluene (20 ml). The mixture was stirred at room temperature for 2 days then partitioned between aqueous sodium bicarbonate solution and dichloromethane. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of methanol/dichloromethane (1:9) to afford the title compound (0.81 g, 23%); MS(ES−) m/e 318 [M−H]−.

Provenance & Evidence