Ammonium Chloride → HCID 178482534, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-((2Z)-3-methyl-2-(methylimino)-2,3-dihydro-1,3-thiazol-5-yl)piperidine-1-carboxylate (5.0 g) obtained in Example 46a) in THF (75 mL) was added n-butyllithium (24 mL, a 1.6 M hexane solution) at −78° C. The reaction solution was mixed for 15 minutes, and then DMF (5 mL) was added thereto, and the mixture was further mixed for 30 minutes. To the reaction solution was added a saturated aqueous ammonium chloride solution, and then poured into a mixed solution of ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic layer was collected by separation, washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified with a silica gel column to give the title compound (3.45 g) as a yellow solid.

Provenance & Evidence