Trimethylsilyldiazomethane → HCID 18723536, compound

Participants

Reaction Steps

To a solution of 0.037 g (0.08 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-carboxypyrrolidine in 0.6 mL of MeOH and 1.2 mL of THF at rt was added 0.2 mL (0.4 mmol) of TMSCHN2 (2M in hexanes) and the reaction mixture was stirred for 6 h. The reaction mixture was concentrated and the residue was purified by chromatography (silica, acetone:hexanes, 1:3) to give the title compound. 1H NMR (CDCl3) δ (key peaks) 7.87-7.91 (m, 3H), 7.47-7.56 (m, 4H), 7.15-7.18 and 7.08-7.11 (m, 2H), 6.98 and 6.95 (t, 2H, J=8.5 Hz),3.79 and 3.62 (s, 3H1); Mass Spectrum (ESI) m/e=475 (M+1).

Provenance & Evidence