Dichloromethane → HCID 18723505, compound

Participants

Reaction Steps

A solution of 0.062 g (0.14 mmol) of Ph3Bi (Aldrich) in 1 mL of CH2Cl2 and 0.65 mL of THF at rt was added 0.027 mL (0.18 mmol) of trifluoroacetic acid and the reaction mixture was stirred for 10 min. This solution was added to a solution of 0.046 g (0.1 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-hydroxyethylpyrrolidine in 1 mL of CH2Cl2. To this reaction mixture was added 0.0083 g (0.046 mmol) of Cu(OAc)2 and the reaction mixture was stirred at 40° C. for 72 h. The reaction mixture was filtered through a thin pad of silica (acetone:hexanes, 1:2) and the filtrate was concentrated. The residue was purified by chromatography (silica, Waters RCM 25×100 with (0.1% iPr2NH in methyl tbutyl ether):hexane=2.25:7.0) to give the title compound. 1H NMR (CDCl3) δ (key peaks) 7.88-7.92 (m, 3H), 7.47-7.56 (m, 4H), 7.23-7.34 (m, 2H), 7.07-7.18 (m, 2H), 6,92-7.01 (m, 4H), 6.80 (d, 1H, J=7.5 Hz), 5.12 (S, 2H). Mass Spectrum (ESI) m/e=523 (M+1).

Provenance & Evidence