Isopropyl chloroformate → HCID 131729851, compound

Participants

Reaction Steps

Palladium hydroxide (300 mg) was added to a methanol (5 mL)/ethyl acetate (5 mL) mixed solution of the benzyl rac-cis-2-methyl-4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate (271 mg, 0.519 mmol) produced in Example 112, and the mixture was stirred for 2 hours in a hydrogen atmosphere. The reaction solution was filtered through Celite (trade name), and the solvent was distilled off under reduced pressure. To a dichloromethane (10 mL) solution of the obtained residue, diisopropylethylamine (447 μL, 2.63 mmol) and isopropyl chloroformate (218 μL, 1.56 mmol) were added at 0° C., and the mixture was stirred for 30 minutes with heating to room temperature. To the reaction solution, a saturated aqueous solution of ammonium chloride was added, followed by extraction with ethyl acetate three times. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3-3:2, V/V) to obtain the title compound as white powder (39.8 mg, yield: 16%).

Provenance & Evidence