p-Fluoronitrobenzene → HCID 22220480, compound

Participants

Reaction Steps

Ammonium formate (15.1 g, 246 mmol) was added to a solution of 1-benzhydryl-3-(tert-butyl-dimethyl-silanyloxy)-azetidine (which was obtained in Example 395) (8.7 g, 24.6 mmol) and 10%Pd/C (1 g) in methanol (100 mL). The reaction was stirred for 3 hours at room temperature. The solution was passed through celite and concentrated to afford a crude solid. The crude solid was taken up in pyridine (75 mL) and the salts were removed by filtration. 4-Fluoronitrobenzene (2.9 mL, 27.1 mmol) was added to the above solution and the reaction was stirred at reflux overnight. Pyridine was removed by vacuum distillation and the resultant crude was treated with water (100 mL), followed by extraction with ethyl acetate (3×25 mL). The organic layers were combined, dried (Na2SO4), filtered, and passed through a plug of silica. The solvent was evaporated and triturated with hexanes to give 3.91 g of the desired product as red solid; 1H NMR (300 MHz, CDCl3) δ1.62 (s, 1H), 3.89(m, 2H), 4.31 (m, 2H), 4.87(m, 1H), 6.31(d, 2H, J=7.14), 8.09(d, 2H, J=7.14 Hz); MS (ES) m/z: 194.8 (MH+); Anal. Calcd. for C9H10N2O3: C, 5.67; H, 5.19; N, 14.43. Found: C, 55.67; H, 5.05; N, 14.59.

Provenance & Evidence