Methyl iodide → HCID 18416133, compound

Participants

Reaction Steps

This compound was prepared by General Method 16 from (±)-2,3-dihydro-2-(hydroxymethyl)-7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinoline (EXAMPLE 28) (10 mg, 0.024 mmol), NaH (4.7 mg, 0.12 mmol) and iodomethane (17 mg, 0.12 mmol) in 0.6 mL THF to afford 8.3 mg (81%) of (±)-2,3-dihydro-7-isopropoxy-2-(methoxymethyl)-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinoline, a yellow solid, after flash chromatography (5:1 hexanes:EtOAc). Data for (±)-2,3-dihydro-7-isopropoxy-2-(methoxymethyl)-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinoline: Rf 0.21 (3:1 hexanes: EtOAc); 1H NMR (400 MHz, CDCl3) δ 7.29 (s, 1H), 7.14 (broad s, 1H), 7.00 (s, 1H), 5.48 (hept, 1H, J =6.2), 4.43 (dd, 1H, J=11.0, 1.6), 4.16 (dd, J=11.0, 2.6), 3.98-4.21 (m, 2H), 3.67-3.73 (m, 1H), 3.50-3.60 (m, 2H), 3.37 (s, 3H), 1.38 (d, 6H, J=6.2).

Provenance & Evidence