تفاعل #58451

معادلة التفاعل

2-bromoacetophenone

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

sodium carbonate

→

title compound

المردود 74.2%

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

المردود 74.2%

المذيبات

ethanol

water

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر