4-Methylmorpholine → HCID 86605650, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinoline-6-carboxylic acid (4.48 g, 10 mmol) in tetrahydrofuran (50 ml) were added dropwise ethyl chlorocarbonate (1.6 ml, 15-mmol) and N-methylmorpholine (1.6 ml, 15 mmol) at 0° C., and after the completion of the dropwise addition, the mixture was stirred at 0° C. for 10 min. Sodium tetrahydroborate (1.32 g, 35 mmol) and methanol (10 ml) were added to the reaction mixture and the mixture was stirred at room temperature for 6 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was crystallized from tetrahydrofuran-diisopropyl ether to give tert-butyl [6-(hydroxymethyl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methylcarbamate (2.42 g, yield 55%) as white crystals.

Provenance & Evidence