Water → 2-(4-Bromophenyl)-5,8-dioxaspiro[3.4]octan-2-amine

Participants

Reaction Steps

To a solution of Compound [XXXIV] (8.40 g, 26.9 mmol, 1.0 eq.) in CH3CN (26 mL) and water (26 mL) was added [bis(trifluoroacetoxy)iodo]benzene (17.4 g, 40.4 mmol, 1.5 eq.) and the resulting mixture stirred at room temperature. After 16 hours the reaction was slowly poured into NaHCO3 (aq sat) and extracted with ethyl acetate (×3). The combined organic layers were dried, concentrated, and the residue purified by silica gel chromatography by eluting with CHCl3 to CHCl3/MeOH/NH4OH (95:5:1) to give Compound [XXXV]: 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm 2.40-2.50 (m, 2H) 2.73-2.82 (m, 2H) 3.77-3.85 (m, 2H) 3.85-3.93 (m, 2H) 7.37-7.44 (m, 2H) 7.45-7.52 (m, 2H).

Provenance & Evidence