Toluene → HCID 58762517, compound

Participants

Reaction Steps

To a refluxing solution of N-methylaniline (0.115 mL, 1.1 mmol) and rhodium (II) acetate (9.4 mg) in toluene (1.6 mL) was added 6-[2-(3-chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-3-diazo-dihydro-pyran-2,4-dione (0.080 g, 0.213 mmol) from Step 1 below over 1Hour. The reaction was stirred at reflux for three more hours. The reaction was concentrated by rotary evaporation, and then purified by preparatory HPLC to give the desired product (28 mg, 29% yield). 1H NMR (CDCl3) δ: 1.48-1.78 (m, 8H), 1.92-2.07 (m, 2H), 2.38 (p, J=8.10 Hz, 1H), 2.51-2.63 (m, 3H), 2.90 (d, J=17.90 Hz, 1H), 3.10 (s, 3H), 3.82 (s, 3H), 6.77-6.81 (m, 2H), 6.86 (t, J=7.44 Hz, 1H), 6.94 (dd, J1=8.38 Hz, J2=1.98 Hz, 1H), 7.10 (d, J=2.07 Hz), 7.18-7.23 (m, 2H), 7.29 (s, 1H).

Provenance & Evidence