Methyl iodide → HCID 18388399, compound

Participants

Reaction Steps

A solution of 0.026 g (0.057 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(1-hydroxyethyl)pyrrolidine (diastereomer 2), 0.012 mg (0.23 mmol) of KOH and 0.0042 mL (0.068 mmol) of methyliodide in 1 mL of DMSO was stirred at rt for 30 min. The reaction mixture was diluted with ether and washed with sat'd NaHCO3 and NaCl solutions. The organic fraction was dried over Na2SO4, filtered and the filtrate was concentrated and purified by chromatography (silica, hexanes:ethylacetate:(2N NH3 in MeOH), 10:10:1) to give the title compound. 1H NMR (CDCl3) δ (key peaks) 7.88-7.91(m, 3H), 7.45-7.55 (m, 4H), 7.20 and 7.10 (d of d, 2H, J=5.5, 8.5 Hz), 7.00 and 6.95 (t, 2H, J=9.0 Hz), 3.40 and 3.24 (s, 3H) 1.25 and 1.02 (d, 3H, J=6.5 Hz), Mass Spectrum (ESI) m/e=475 (M+1).

Provenance & Evidence