反应详情

温度

40 °C

Triethylamine (8.56 mL, 0.061 mol) and tert-butyl 2-bromoethylcarbamate (see Preparation R above, 11.0 g, 0.049 mol) were added to a solution of 4-{[(2S)-2-hydroxy-3-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)-propyl]oxy}benzonitrile (see preparation B above, 12.41 g, 0.038 mol) in DMF (100 mL). The mixture was stirred for 20 h at 40° C., then concentrated in vacuo. The residue was dissolved in chloroform (100 mL), and washed with saturated sodium chloride. The aqueous layer was separated and extracted with chloroform (2×150 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The crude brown oil was chromatographed (×2) on silica gel, eluting first with chloroform:methanol (9:1), then with chloroform:methanol:conc. ammonium hydroxide (9:1:0.05) to afford 4.13 g (24%) of the title compound.

1. concentrationconcentrated in vacuo
2. dissolutionThe residue was dissolved in chloroform (100 mL)
3. washwashed with saturated sodium chloride
4. customThe aqueous layer was separated
5. extractionextracted with chloroform (2×150 mL)
6. dry with materialThe combined organic layers were dried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customThe crude brown oil was chromatographed (×2) on silica gel
9. washeluting first with chloroform:methanol (9:1)