反应详情

温度

50 °C

Add successively 21 mL of water, 1.12 g (22.8 mmol) of sodium cyanide, 4.52 mL (54.27 mmol) of 12N aqueous ammonia solution and 2.32 g (43.41 mmol) of NH4Cl to a solution of 3 g (21.7 mmol) of bicyclo[3.3.1]nonan-9-one in 40 mL of EtOH. Stir the reaction mixture for 18 h at 50° C. Then add 5 mL of 12N aqueous ammonia solution and heat the mixture again for 4 h at 50° C. Cool the solution to RT then distribute in 100 mL of a 1:1 mixture of ether/1N aqueous soda solution. After extraction, wash the organic phase with 3×50 mL of water, dry over Na2SO4 and concentrate under reduced pressure. Take up the residue obtained in 50 mL of ether and then treat for 1 minute with a gentle stream of hydrogen chloride. Filter the hydrochloride thus obtained, wash with 20 mL of ether and distribute in 100 mL of a 1:1 mixture of DCM/saturated aqueous solution of Na2CO3. Extract the aqueous phase again with 50 mL of DCM, then combine the organic phases, wash with 2×20 mL of water and dry over Na2SO4. After concentration under reduced pressure, we obtain 1.88 g of 9-aminobicyclo[3.3.1]nonane-9-carbonitrile in the form of oil.

1. temperatureheat the mixture again for 4 h at 50° C
2. temperatureCool the solution to RT
3. extractionAfter extraction
4. washwash the organic phase with 3×50 mL of water
5. dry with materialdry over Na2SO4
6. concentrationconcentrate under reduced pressure
7. customobtained in 50 mL of ether
8. filtrationFilter the hydrochloride
9. customthus obtained
10. washwash with 20 mL of ether
11. additiondistribute in 100 mL of a 1:1 mixture of DCM/saturated aqueous solution of Na2CO3
12. extractionExtract the aqueous phase again with 50 mL of DCM
13. washwash with 2×20 mL of water
14. dry with materialdry over Na2SO4
15. concentrationAfter concentration under reduced pressure, we