Hydrochloric Acid → HCID 60128225, compound

Temperature

-5 °C

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.

1. extractionThe mixture was extracted with dichloromethane
2. dry with materialtwice, and the combined organic extracts were dried (MgSO4)
3. customevaporated under reduced pressure
4. customto give a white solid
5. stirringthe reaction stirred overnight at room temperature
6. customThe mixture was evaporated under reduced pressure
7. customthe residue purified by column chromatography

ORD record

ord-3a4607a498ff4e0198a1ca37582c087d

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06831074B2