Réaction #167981

Équation de réaction

NaH

(S)-diethyl 3,3′-((1-phenylethyl)azanediyl)dipropanoate

→

(5)-ethyl 4-oxo-1-((S)-1-phenylethyl)piperidine-3-carboxylate

Solvants

THF

water

EtOAc

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas then added dropwise
2. 2
   Températurewarmed to 60° C.
3. 3
   Températureheated for 3 h
4. 4
   Autrethe organic layer was then separated
5. 5
   Séchagedried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   AutreThe residue was purified by FCC (5-7% EtOAc/hexanes)

Mode opératoire

A suspension of NaH (2.24 g, 93.4 mmol) in THF (20 mL) was cooled to 0° C. and as solution of (S)-diethyl 3,3′-((1-phenylethyl)azanediyl)dipropanoate (15 g, 46.7 mmol) in THF was then added dropwise. The reaction mixture was allowed to warm to rt and then warmed to 60° C. and heated for 3 h. The mixture was diluted with water and EtOAc and the organic layer was then separated, dried (Na2SO4), filtered and concentrated. The residue was purified by FCC (5-7% EtOAc/hexanes) to give (5)-ethyl 4-oxo-1-((S)-1-phenylethyl)piperidine-3-carboxylate.

Source