Ammonium Chloride → HCID 15341130, compound

Participants

Reaction Steps

4.70 ml (11.78 mmol) of a 2.5M solution of n-butyllithium in n-hexane are slowly added to a stirred solution, cooled to -78° C., of 3.28 g (11.78 mmol) of 6-benzyloxycarbonylamino-quinoline and 1 mg of 1,10-phenanthroline hydrate in 30 ml of anhydrous THF until the colour changes. Thereafter, 1.67 ml (11.78 mmol) of (R)-glycidyl butyrate are added dropwise and the reaction mixture is allowed to warm to room temperature in the course of 16 hours. 30 ml of saturated aqueous NH4Cl solution are then added dropwise in the course of 15 minutes. The aqueous phase is extracted with 3×60 ml of ethyl acetate and the organic phases are combined, washed with 2×50 ml of NaCl solution and dried over MgSO4. Evaporation of the solvent in vacuo, tritration of the residue with ether and recrystallization from 25 ml of ethanol gives 1.30 g (45%) of the title compound as colourless crystals.

Provenance & Evidence