Реакция #58451

Уравнение реакции

2-bromoacetophenone

2-Carboxymethyl-piperidine-1-carboxylic acid tert butyl ester

sodium carbonate

→

title compound

Выход 74.2%

(RS)-2-(2-Oxo-2-phenyl-ethoxycarbonylmethyl)-piperidine-1-carboxylic acid tert butyl ester

Выход 74.2%

Растворители

ethanol

water

Условия реакции

Обработка

1. 1
   workup.WAITstood for 16 h
2. 2
   workup.WAITThe mixture was again boiled for 2 h.
3. 3
   Другоеsolvent removed at reduced pressure
4. 4
   Другоеthe residue partitioned between water and ethyl acetate
5. 5
   СушкаThe organic phase was dried (MgSO4) and solvent
6. 6
   Другоеremoved at reduced pressure
7. 7
   Другоеchromatographed (silica gel, 1:1 ethyl acetate:pentane)

Методика

2-Carboxymethyl-piperidine-1-carboxylic acid tert butyl ester (2.86 g) and sodium carbonate (0.62 g) were dissolved in water (30 ml) using gentle warming. A solution of 2-bromoacetophenone (2.33 g) in ethanol (60 ml) was then added and the mixture boiled for 2 h. the mixture was cooled to room temperature and stood for 16 h. The mixture was again boiled for 2 h. solvent removed at reduced pressure and the residue partitioned between water and ethyl acetate. The organic phase was dried (MgSO4) and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, 1:1 ethyl acetate:pentane) to give the title compound (3.14 g).

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