Réaction #59637

Équation de réaction

dimethylamine

HOBT

DCC

(2S)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid

ether

→

expected product

(2S)-N,N-Dimethyl-2-(tert-butoxycarbonyl)-piperidine-2-carboxamide

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   workup.WAITthe mixture is left
2. 2
   TempératureThe reaction mixture is cooled on an ice bath
3. 3
   Autreby bubbling for two times 10 minutes
4. 4
   workup.WAITthe mixture is then left
5. 5
   workup.STIRRINGstirring overnight at RT
6. 6
   FiltrationAn insoluble material is filtered off
7. 7
   Concentrationthe filtrate is concentrated under vacuum
8. 8
   AutreThe residue is chromatographed on silica gel
9. 9
   Lavageeluting with a gradient of a DCM/MeOH mixture of from (98/2; v/v) to (96/4; v/v)
10. 10
    AutreThe product obtained
11. 11
    Filtrationthe precipitate is spin-filtered off

Mode opératoire

6.2 g of HOBT and then 9.45 g of DCC are added at RT to a solution of 10 g of (2S)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (commercial) in 130 ml of DCM, and the mixture is left stirring for 1 hour. The reaction mixture is cooled on an ice bath, dimethylamine gas is added by bubbling for two times 10 minutes and the mixture is then left stirring overnight at RT. An insoluble material is filtered off and the filtrate is concentrated under vacuum. The residue is chromatographed on silica gel, eluting with a gradient of a DCM/MeOH mixture of from (98/2; v/v) to (96/4; v/v). The product obtained is taken up in ether and the precipitate is spin-filtered off. 8.5 g of the expected product are obtained.

Source