1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-[(1S)(4S)-2-benzyl-2,5-diazabicyclo{2,2,1}heptan-5-yl]-3-fluoro-1-nitrobenzene

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Reaction Steps

A mixture of (1S)(4S)-2-benzyl-2,5-diazabicyclo{2,2,1}heptane dihydrobromide [Henry et al. J. Med. Chem. (1974), 17, 481] (1.05 g, 3 mmol), 3,4-difluoronitrobenzene (0.48 g, 3 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (1.38 g, 9 mmol) in acetonitrile (10 ml) was stirred and heated at reflux for 2 hours. Solvent was evaporated and the residue was partitioned between EtOAc and water. The organic layer was filtered (1PS paper) and the filtrate evaporated to give 4-[(1S)(4S)-2-benzyl-2,5-diazabicyclo{2,2,1}heptan-5-yl]-3-fluoro-1-nitrobenzene (0.95 g, 97%) as a solid. MS: 328 (M+); NMR(CDCl3); 1.82-2.07 (2H, dd); 2.77-2.98 (2H, dd); 3.59 (2H+1H, s); 3.72 (2H, s); 3.91 (1H, m); 4.58 (1H, s); 6.6 (1H, t); 7.2-7.34 (5H+CHCl3);

Provenance & Evidence