反応 #58451

反応方程式

2-bromoacetophenone

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

sodium carbonate

→

title compound

収率 74.2%

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

収率 74.2%

溶媒

ethanol

water

反応条件

後処理

1. 1
   workup.WAITstood for 16 h
2. 2
   workup.WAITThe mixture was again boiled for 2 h.
3. 3
   その他solvent removed at reduced pressure
4. 4
   その他the residue partitioned between water and ethyl acetate
5. 5
   乾燥The organic phase was dried (MgSO4) and solvent
6. 6
   その他removed at reduced pressure
7. 7
   その他chromatographed (silica gel, 1:1 ethyl acetate:pentane)

実験手順

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).

出典