Pyridine → HCID 68805308, compound

Temperature

0 °C

Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (2.1 g, 9.8 mmol) was dissolved in 100 mL dry diethyl ether under an argon atmosphere, added dry pyridine (3.3 mL, 32.5 mmol), cooled to 0° C. then added oxalyl chloride (1.4 mL, 16.3 mmol) dropwise. A precipitate forms immediately upon addition of oxalyl chloride and therefore reaction requires vigorous stirring. Stirred at 0° C. for one hour than at ambient temperature for 2 hours. Dry diethyl ether (100 mL) was added and the solids were filtered off, washing with more diethyl ether. The filtrates were concentrated, then redissolved in dry DCM under argon, cooled to 0° C., added 1 mL dry pyridine then added 4-amino-benzonitrile (0.96 g, 8.1 mmol) in one portion. Stirred at ambient temperature for 2 hours, concentrated, redissolved in ethyl acetate (250 mL), washed with 10% citric acid (3×100 mL), water, brine, dried with MgSO4, filtered and concentrated to yield title compound as a white foam. (2.4 g, 93%) APCI (AP−): 314.1 (M−H)−.

1. customreaction
2. filtrationthe solids were filtered off
3. washwashing with more diethyl ether
4. concentrationThe filtrates were concentrated
5. dissolutionredissolved in dry DCM under argon
6. temperaturecooled to 0° C.
7. additionadded 1 mL dry pyridine
8. stirringStirred at ambient temperature for 2 hours
9. concentrationconcentrated
10. dissolutionredissolved in ethyl acetate (250 mL)
11. washwashed with 10% citric acid (3×100 mL), water, brine
12. dry with materialdried with MgSO4
13. filtrationfiltered
14. concentrationconcentrated

ORD record

ord-03afd24323f246c89ce55247ac9c2fc5

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07030141B2