Ammonium Chloride → HCID 67479833, compound

To a stirred solution of (R)-tert-butyl 3-(5-chloro-3-nitropyridin-2-ylamino)pyrrolidine-1-carboxylate (802 mg, 2.34 mmol) in MeOH (25 mL) and water (25 mL) were added iron dust (2.00 g, 35 mmol) and NH4Cl (1.25 g, 2.4 mmol). The mixture was heated at reflux for 6 h and filtered through Celite, washing with EtOAc. The filtrate was concentrated and the residue was dissolved in CH2Cl2 (150 mL) and 1 M aq NaOH (50 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (50 mL). The combined CH2Cl2 layer was washed with brine (50 mL), dried over Na2SO4 and concentrated to leave (R)-tert-butyl 3-(3-amino-5-chloropyridin-2-ylamino)pyrrolidine-1-carboxylate (680 mg, 93%) as a black solid. LC-MS Method 1 tR=1.28 min, m/z=313, 257.

1. temperatureThe mixture was heated
2. temperatureat reflux for 6 h
3. filtrationfiltered through Celite
4. washwashing with EtOAc
5. concentrationThe filtrate was concentrated
6. dissolutionthe residue was dissolved in CH2Cl2 (150 mL)
7. customThe layers were separated
8. extractionthe aqueous layer was extracted with CH2Cl2 (50 mL)
9. washThe combined CH2Cl2 layer was washed with brine (50 mL)
10. dry with materialdried over Na2SO4
11. concentrationconcentrated

ORD record

ord-5821fa4a027e484d89de0d4cdf7eb97d

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09163012B2