Ethanol → 4-(4-Amino-3-cyclohept-1-enyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A solution of 230 mg (0.647 mmol) 4-(4-amino-3-bromo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (as prepared in the previous step) in 6 mL toluene and 3 mL EtOH was treated with 118 mg (0.842 mmol) cyclohept-1-enylboronic acid and 2.60 mL (5.18 mmol) 2.0 M Na2CO3. The mixture was degassed via sonication, placed under Ar, treated with 52.3 mg (0.0453 mmol) Pd(PPh3)4, and heated to 85° C. for 23 h. The mixture was diluted with EtOAc (15 mL) and washed with water (1×15 mL) and brine (1×15 mL). The combined aqueous layers were extracted with EtOAc (15 mL), and the combined organic layers were dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a Varian MegaBond Elut 50-gm column with 10-18% EtOAc-hexane afforded 108 mg (45%) of the title compound as a tan solid: Mass spectrum (ESI, m/z): Calcd. for C19H27N2O2, 315.2 (M−C4H9+2H), found 315.2.

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