Potassium Carbonate → (2R)-2-methyl-1-[2-(4-nitrophenyl)ethyl]pyrrolidine

(2R)-2-Methylpyrrolidine L-tartrate (4.0 g, 17.0 mmol), 1-(2-bromoethyl)-4-nitrobenzene (9.8 g, 43 mmol), and potassium carbonate (12 g, 85 mmol), were combined in DMF (20 mL) in a sealed tube at 50° C. and stirred vigorously for 16 hours. The mixture was allowed to cool to room temperature, diluted with diethyl ether (100 mL), washed with water (2 times, 100 mL and then 50 mL), and extracted with 1 M HCl (2 times, 50 mL and 25 mL). The aqueous acidic extractions were combined, washed with diethyl ether (50 mL), cooled to 0° C., adjusted to pH 14 with 50% NaOH solution, and extracted with dichloromethane (3 times, 50 mL). The dichloromethane extractions were combined, dried (MgSO4), filtered, and the filtrate concentrated to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 1.08 (d, J=6 Hz, 3H), 1.43 (m, 1H), 1.75 (m, 2H), 1.93 (m, 1H), 2.19 (q, J=9 Hz, 1H), 2.34 (m, 2H), 2.91 (m, 2H), 3.03 (m, 1H), 3.22 (td, J=8, 3 Hz, 1H), 7.38 (d, J=9 Hz, 2H), 8.15 (d, J=9 Hz, 2H); MS (DCI/NH3) m/z 235 (M+H)+.

1. washwashed with water (2 times, 100 mL
2. extraction50 mL), and extracted with 1 M HCl (2 times, 50 mL and 25 mL)
3. extractionThe aqueous acidic extractions
4. washwashed with diethyl ether (50 mL)
5. temperaturecooled to 0° C.
6. extractionextracted with dichloromethane (3 times, 50 mL)
7. extractionThe dichloromethane extractions
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationthe filtrate concentrated

ORD record

ord-1ed6b620bfef4cf98badd999f144471c

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07153889B2