Triethylamine → HCID 67017898, compound

Participants

Reaction Steps

To a stirred mixture of 1-[(benzyloxy)methyl]tricyclo[3.3.1.03,7]nonane-3-carboxylic acid (1.8 g, 6.3 mmol) obtained in step III, triethylamine (2.6 mL, 18.9 mmol) and toluene (25 mL) at ice bath temperature was added diphenylphosphoryl azide (1.5 mL, 6.93 mmol). The reaction mixture was warmed to r.t, stirred for one hour, and then refluxed for 4 h. Upon completion of the reaction, the reaction mixture was transferred to a separatory funnel and washed with water. The organic layer was stirred with aq. KOH solution (50% w/v, 12.6 mL), and nBu4NI (120 mg, 0.32 mmol) for 2 h. The reaction mixture was cooled to ice bath temperature, acidified with 2N KHSO4 to pH 2, extracted with ether, the aqueous layer was basified with aq. NaOH solution (50% w/v) and extracted with chloroform. The combined organic layers were dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure to obtain 1-[(benzyloxy)methyl]tricyclo[3.3.1.03,7]nonan-3-amine (0.82 g) as viscous liquid in 51% yield. m/z (M+1) 258; 1H NMR (CDCl3) 300 MHz δ 7.37-7.24 (m, 5H), 4.50 (s, 2H), 3.24 (s, 2H), 2.37-2.29 (m, 1H), 2.0-1.81 (m, 3H), 1.78-1.70 (m, 1H), 1.70-1.45 (m, 7H), 1.40 (dd, J=2.9, 10.7 Hz, 1H).

Provenance & Evidence