反应详情

To a solution of the product of Example 36, Step A (0.15 g, 0.6 mmol) in MeOH (3 m) NaBH4 (0.028 g; 0.74 mmol) was added in portion wise at room temperature. After 1 h of stirring the solvent was evaporated and the residue was diluted to 20 ml with EtOAc and washed with H2O. The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue (0.25 g, 0.99 mmol) was dissolved in anhydrous THF (5 ml). To this DIPEA (0.19 ml, 1.1 mmol) was added at 0° C. under N2, with stirring, followed by SOCl2 (0.08 ml, 1.1 mmol). This was stirred overnight at room temperature. The solvent was distilled off and the crude product was diluted to 20 ml with EtOAc and washed with NaHCO3 solution. The organic layer was separated, dried over MgSO4 and filtered. The filtrate was passed through silica gel bead and washed with fresh EtOAc (20 ml). The combined filtrates were evaporated to dryness to give the title compound (0.24 g, 89%) as colourless oil. 1H-NMR (CDCl3) 4.64 (s, 2H); 7.30 (d, 3H, J=8.12 Hz); 7.4-7.58 (m, 4H); 7.73 (d, 2H, J=7.84 Hz).

1. customwas evaporated
2. additionthe residue was diluted to 20 ml with EtOAc
3. washwashed with H2O
4. customThe organic layer was separated
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customThe filtrate was evaporated to dryness
8. stirringwith stirring
9. stirringThis was stirred overnight at room temperature
10. distillationThe solvent was distilled off
11. additionthe crude product was diluted to 20 ml with EtOAc
12. washwashed with NaHCO3 solution
13. customThe organic layer was separated
14. dry with materialdried over MgSO4
15. filtrationfiltered
16. washwashed with fresh EtOAc (20 ml)
17. customThe combined filtrates were evaporated to dryness