Реакция #73836

Уравнение реакции

4-chloro-3-fluorophenylmagnesium bromide

4-oxo-piperidine-1-carboxylic acid tert-butyl ester

ammonium chloride

→

title compound

Выход 30.4%

4-(4-Chloro-3-fluoro-phenyl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Выход 30.4%

Условия реакции

Обработка

1. 1
   Другоеthe organic solvent was removed in vacuo
2. 2
   ЭкстракцияThe mixture was extracted with ethyl acetate
3. 3
   Промывкаthis extract was washed with brine
4. 4
   Сушкаdried (MgSO4)
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated
7. 7
   Другоеto afford a residue which
8. 8
   Другоеwas purified by column chromatography (SiO2)
9. 9
   Промывкаeluting with gradient of ethyl acetate/petrol (0% to 20%)

Методика

A solution of 4-chloro-3-fluorophenylmagnesium bromide (15 ml, 7.5 mmol, 0.5M in THF) was added, under nitrogen, to 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (1.02 g, 5.1 mmol). After 24 hours, saturated ammonium chloride solution was added then the organic solvent was removed in vacuo. The mixture was extracted with ethyl acetate, then this extract was washed with brine, dried (MgSO4), filtered and concentrated to afford a residue which was purified by column chromatography (SiO2), eluting with gradient of ethyl acetate/petrol (0% to 20%) to afford the title compound (511 mg, 30%). 1H NMR (Me-d3-OD) δ 1.48 (9H, s), 1.67 (2H, br.d), 1.92 (2H, td), 3.16-3.29 (2H, m), 3.99 (2H, br.d), 7.27 (1H, dd), 7.38 (1H, dd), 7.42 (1H, t).

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