反应详情

温度

-5 °C

4.7 g (47 mmol) DIPEA in THF at −5° C. was treated slowly with 29.1 mL (47 mmol) n-Buli (1.6N in hexane) and stirred for 30 min at −5° C. and subsequently cooled to −75° C. and stirred for 2 h. A solution of 10 g (39 mmol) ethyl 1-tert-butoxycarbonylpiperidine-4-carboxylate (commercially available) in THF was added and the mixture was stirred for 2 h at −75° C. 8.51 g (47 mmol) 1-iodo-2-methylpropane was added and the mixture was allowed to stir to room temperature over night. The mixture was quenched at 0° C. with citric acid 10% aq. and extracted with ethyl acetate. The combined organic layers were washed with NaCl aq. sat., dried with Na2SO4, filtered and evaporated. The residue was purified by column chromatography on silica eluting with a gradient formed heptane and t-butyl-methylether. The combined product fractions were evaporated to yield 10.2 g (84%) of the title compound as light yellow oil. MS (m/e): 331.2 (M+NH4+).

1. temperaturesubsequently cooled to −75° C.
2. stirringstirred for 2 h
3. stirringthe mixture was stirred for 2 h at −75° C
4. stirringto stir to room temperature over night
5. customThe mixture was quenched at 0° C. with citric acid 10% aq.
6. extractionextracted with ethyl acetate
7. washThe combined organic layers were washed with NaCl aq. sat.
8. dry with materialdried with Na2SO4
9. filtrationfiltered
10. customevaporated
11. customThe residue was purified by column chromatography on silica eluting with a gradient
12. customformed heptane and t-butyl-methylether
13. customThe combined product fractions were evaporated