4-Methylmorpholine → HCID 22728145, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(2,6-Dimethyl-4-nitro-phenoxy)-2-methoxy-benzoic acid (2.0 g, 6.3 mmol) in tetrahydrofuran (60 mL) at 0° C. under nitrogen was added N-methylmorpholine (1.4 mL) and isobutyl chloroformate (1.3 g, 9.5 mmol). The resulting mixture was stirred for 25 minutes at 0° C., and cyclobutyl amine (0.9 g, 13 mmol) was added in a single portion at 0° C. The reaction solution was stirred for another 30 minutes at 0° C. and warmed to room temperature over 1 hour. The solution was then concentrated to a viscous oily solid which was partitioned between water (25 mL) and methylene chloride (25 mL). The organic phase was separated and the aqueous phase was extracted with methylene chloride (10 mL). The combined organic extracts were washed with saturated aqueous NaHCO3, 1N hydrochloric acid and brine, dried over Na2SO4, filtered, and concentrated. To the residue was purified by column chromatography (Et2O/methylene chloride/hexane=1/7/12) to afford the title compound (1.67 grams) as a crude product. 1H NMR (400 MHz, CDCl3) δ8.04 (br s, 1H), 7.98 (s, 2H), 7.54 (d, 1H), 6.90 (d, 1H), 6.86 (dd, 1H), 4.51-4.49 (m, 1H), 3.94 (s, 3H), 2.41-2.38 (m, 2H), 2.17 (s, 6H), 1.95-1.90 (m, 2H), 1.80-1.75 (m, 2H). MS (APCI+) Calc: 370.4, Found: 371.2 (M+1).

Provenance & Evidence