反应详情

n-BuLi (2.5 M, 2 mL, 5.21 mmol) was added into a solution of 4-bromo-1,2-dichlorobenzene (1.07 g, 4.74 mmol) in dry THF (10 mL) at −78° C. The mixture was stirred for 20 mins and then a solution of tert-butyl 4-oxopiperidine-1-carboxylate (0.95 g, 4.74 mmol) in THF (5 mL) was added. The mixture was further stirred at −78° C. for 1 h. After this time, the reaction was quenched with NH4Cl (aq., 15 mL), extracted with ethyl acetate (50 mL×3), dried over Na2SO4 and concentrated to yield a residue. The residue was purified by flash chromatography using 10-30% ethyl acetate in hexanes as an eluent to provide tert-butyl 4-(3,4-dichlorophenyl)-4-hydroxypiperidine-1-carboxylate (1.6 g, 90% purity, 88% yield) as a colorless oil. MS found: 346.3 (M+).

1. stirringThe mixture was further stirred at −78° C. for 1 h
2. customAfter this time, the reaction was quenched with NH4Cl (aq., 15 mL)
3. extractionextracted with ethyl acetate (50 mL×3)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. customto yield a residue
7. customThe residue was purified by flash chromatography