Benzene, 1-iodo-4-(trifluoromethyl)- → Tert-butyl({1-[4-(trifluoromethyl)phenyl]piperidin-4-yl}methyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a mixture of sodium tert-butoxide, 1-iodo-4-(trifluoromethyl)benzene (686 μl) and tert-butyl(piperidin-4-ylmethyl)carbamate (1.00 g) in toluene (10 ml) was added 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphine) (286 mg) and tris-dibenzylideneacetone palladium(0) (211 mg). The mixture was heated to 90° C. for 15 h. The mixture was cooled to room temperature, concentrated in vacuo, and diluted with dichloromethane. This solution was filtered through a short plug of silica gel and concentrated. The residue was purified via flash chromatography on a Biotage Horizon, 40M column, eluting with 10 column volumes of 33% ethyl acetate in hexanes to provide 1.36 g (81%) of the title compound. Mass spectrum (ESI) 303.0 (M+1).

Provenance & Evidence