Triethylamine → HCID 66632624, compound

To a stirred solution of 1-(bromomethyl)-2-fluoro-3-nitrobenzene (2.00 g, 8.54 mmol) and pyrrolidine (0.91 g, 12.82 mmol) in CH2Cl2 (15 mL) was added triethylamine (1.72 g, 17.08 mmol) dropwise at 0° C. The mixture was stirred at room temperature overnight and then evaporated to dryness under reduced pressure. The residue was diluted with water (15 mL) and extracted with EtOAc (2×30 mL). The EtOAc solution was washed with brine (20 mL), dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel using a mixture of EtOAc and hexane as eluent to give 1-(2-fluoro-3-nitrobenzyl)pyrrolidine (1.20 g, 63%) as a viscous oil. 1H NMR (400 MHz, CD3OD): δ 8.02-7.97 (m, 1H), 7.81-7.76 (m, 1H), 7.36 (td, 1H, J=8.0, 1.2 Hz), 3.81 (d, 1H, J=2.0 Hz), 2.62-2.58 (m, 4H), 1.84-1.80 (m, 4H).

1. customevaporated to dryness under reduced pressure
2. additionThe residue was diluted with water (15 mL)
3. extractionextracted with EtOAc (2×30 mL)
4. washThe EtOAc solution was washed with brine (20 mL)
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. customevaporated to dryness under reduced pressure
8. customThe residue was purified by MPLC on silica gel using
9. additiona mixture of EtOAc and hexane as eluent

ORD record

ord-e8343f6e0948421fb0daf4d77d3e4a1b

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080568B1