Hydrochloric Acid → HCID 45792670, compound

Glutaraldehyde (36.5 mL, 95 mmol) and 1,3-acetonedicarboxylic acid (10 g, 65 mmol) were suspended in water (100 mL) and stirred by a mechanical stirrer under argon for 30 min. To the yellow solution cyclopropylamine (3.5 mL, 50 mmol) were added in one portion whereby a slightly exothermic reaction occurred and a gas evolved. The reaction mixture was stirred at 23° C. overnight. The reaction mixture was acidified with 3 N Hydrochloride solution until pH<2, then extracted with dichloromethane. The water layer was now adjusted with 3 N NaOH to pH 8 and extracted three times with dichloromethane, the organic layers were combined, dried over MgSO4, filtered and the solvents were evaporated. Purification of the crude product by flash chromatography with n-heptane and ethyl acetate gave the title compound as a white solid (940 mg, 11%); MS: m/e=180.2 (M+H+).

1. customa slightly exothermic reaction
2. stirringThe reaction mixture was stirred at 23° C. overnight
3. extractionextracted with dichloromethane
4. extractionextracted three times with dichloromethane
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customthe solvents were evaporated
8. customPurification of the crude product by flash chromatography with n-heptane and ethyl acetate

ORD record

ord-1a3b778985cb4b6d9b5cd9742cba2844

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08183380B2