反应详情

To an ice-cooled suspension of LAH (1.43 g, 35.7 mmol, 1.5 eq.) in dry Et2O (70.0 mL) under N2, a solution of 2-methyl-2-phenyl-propionitrile (3.46 g, 23.8 mmol, 1.0 eq.) in dry Et2O (3.0 mL) was added dropwise over 30 min. After 30 min the cooling bath was removed and the mixture was stirred at r.t. for 3 hours. The mixture was again cooled to 0° C. and carefully quenched by the dropwise addition of iPrOH (35 mL) and then 2M aq. NaOH (20 mL). The resulting suspension was filtered through celite and the filter cake was rinsed with THF. The fitrate was concentrated in vacuo. The residue was partitioned between DCM (125 mL) and 1M aq. NaOH (125 mL). The layers were separated and the aq. phase was extracted with DCM (2×50 mL). The comb. org. phases were washed with sat. aq. NaCl soln. (1×25 mL), dried over MgSO4, and concentrated in vacuo. The resulting 2-methyl-2-phenyl-propylamine was used without further purification.

1. customAfter 30 min the cooling bath was removed
2. temperatureThe mixture was again cooled to 0° C.
3. customcarefully quenched by the dropwise addition of iPrOH (35 mL)
4. filtrationThe resulting suspension was filtered through celite
5. washthe filter cake was rinsed with THF
6. concentrationThe fitrate was concentrated in vacuo
7. customThe residue was partitioned between DCM (125 mL) and 1M aq. NaOH (125 mL)
8. customThe layers were separated
9. extractionthe aq. phase was extracted with DCM (2×50 mL)
10. washphases were washed with sat. aq. NaCl soln
11. dry with material(1×25 mL), dried over MgSO4
12. concentrationconcentrated in vacuo
13. customThe resulting 2-methyl-2-phenyl-propylamine was used without further purification