Triethylamine → HCID 67017898, compound

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).

1. temperatureThe reaction mixture was warmed
2. temperaturerefluxed for 4 h
3. customUpon completion of the reaction
4. customthe reaction mixture was transferred to a separatory funnel
5. washwashed with water
6. temperatureThe reaction mixture was cooled to ice bath temperature
7. extractionextracted with ether
8. extractionextracted with chloroform
9. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
10. customthe solvent was evaporated under reduced pressure

ORD record

ord-b44d9827c5e8461d8c096b4f483e6720

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985759B2