Hydrochloric Acid → 1-Phenyltricyclo[3.3.1.03,7]nonan-3-amine

Participants

Reaction Steps

To a stirred solution of 1-phenyltricyclo[3.3.1.03,7]nonane-3-carboxylic acid (0.6 g, 2.48 mmol) obtained from step I and triethylamine (1.0 mL, 7.44 mmol) in toluene (10 mL) under N2 atmosphere at ice bath temperature was added diphenylphosphoryl azide (0.64 mL, 3.0 mmol). The reaction mixture was warmed to room temperature and stirred for 1 h, then it was refluxed for 4 h. The reaction mixture was cooled to r.t., washed with water and stirred with aq. KOH solution (50% w/v, 5.0 mL) and nBu4NI (92 mg, 0.25 mmol) for 2 h at r.t. The reaction mixture was cooled to ice bath temperature, acidified with conc. HCl to pH 2, extracted with diethyl ether. The aqueous layer was basified with aq. NaOH solution (50% w/v) and extracted with chloroform. The combined organic layer was dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure to obtain 1-phenyltricyclo[3.3.1.03,7]nonan-3-amine (0.33 g) as viscous liquid in 62% yield. m/z (M+1) 214; 1H NMR (CDCl3) 300 MHz δ 7.40-7.22 (m, 4H), 7.22-7.15 (m, 1H), 2.42-2.35 (m, 1H), 2.20-2.05 (m, 2H), 2.02-1.52 (m, 9H).

Provenance & Evidence