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

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).

1. temperatureit was refluxed for 4 h
2. temperatureThe reaction mixture was cooled to r.t.
3. washwashed with water
4. temperatureThe reaction mixture was cooled to ice bath temperature
5. extractionextracted with diethyl ether
6. extractionextracted with chloroform
7. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
8. customthe solvent was evaporated under reduced pressure

ORD record

ord-be24a43335af4b2b9b741845a4446ba1

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985759B2