Hydrochloric Acid → HCID 60128225, compound

Participants

Reaction Conditions

Reaction Steps

Concentrated hydrochloric acid (6.0 ml) was added to a suspension of (2R,4R)-4-methyl-2-piperidinecarboxylic acid (Biochem. Biophys. Res. Commun. 1981; 101(2); 440) (10 g, 7.03 mmol), in water (30 ml) and this solution cooled to −5° C. A solution of sodium nitrite (5.3 g, 7.7 mmol), in water (20 ml) was then added, and this solution stirred at room temperature for 2 hours. The mixture was extracted with dichloromethane, twice, and the combined organic extracts were dried (MgSO4) and evaporated under reduced pressure to give a white solid. Trifluoroacetic anhydride (11 ml, 7.70 mmol) was added to a cooled (−3° C.) solution of the intermediate product in ether (200 ml) and the reaction stirred overnight at room temperature. The mixture was evaporated under reduced pressure, and the residue purified by column chromatography using ethyl acetate as the eluant. The title compound was obtained as a brown crystalline solid, 7.1 g.

Provenance & Evidence