Reaktion #58451

Reaktionsgleichung

2-bromoacetophenone

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

sodium carbonate

→

title compound

Ausbeute 74.2%

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

Ausbeute 74.2%

Lösungsmittel

ethanol

water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle