反应详情

To a solution of the product of Step C (0.069 g; 0.219 mmol) in AcOH (1 ml) and anhydrous THF (1.5 ml) NaBH3CN (3×0.07 g; 3.34 mmol) was added portion wise over a period of 2 h, while the temperature of the reaction mixture was kept <15° C. The solvents were removed in vacuo and the residue was diluted to 15 ml with EtOAc, washed with 5% NaOH, H2O, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness under reduced pressure. The residue was dissolved in a mixture of CF3CO2H and EtOH (2 ml+2 ml), refluxed for 1 h and re evaporated. The residue was treated with NH4OH saturated CH2Cl2 (5 ml) and evaporated under reduced pressure. The residue was purified by FCC (SiO2, CH2Cl2) to give the title compound (0.034 g; 48%), as colourless solid. 1H-NMR (CDCl3) 0.95 (tr, 3H, J=7.4 Hz); 1.61-1.75 (m, 2H); 1.91-2.0 (m, 2H); 2.66 (tr, 2H, J=7.8 Hz); 3.09 (tr, 2H, J=6.5 Hz); 3.29-3.33 (m, 2H); 3.8 (broad s, 1H); 6.6 (dd, 1H, J=1, 8 Hz); 7.07 (tr, 1H, J=7.9 Hz); 7.3-7.35 (m, 3H); 8.1 (d, 2H, J=8.3 Hz).

1. customwas kept <15° C
2. customThe solvents were removed in vacuo
3. additionthe residue was diluted to 15 ml with EtOAc
4. washwashed with 5% NaOH, H2O, brine
5. dry with materialdried over anhydrous MgSO4
6. filtrationfiltered
7. customfiltrate evaporated to dryness under reduced pressure
8. dissolutionThe residue was dissolved in a mixture of CF3CO2H and EtOH (2 ml+2 ml)
9. temperaturerefluxed for 1 h
10. customre evaporated
11. additionThe residue was treated with NH4OH saturated CH2Cl2 (5 ml)
12. customevaporated under reduced pressure
13. customThe residue was purified by FCC (SiO2, CH2Cl2)