Reaktion #59637

Reaktionsgleichung

dimethylamine

HOBT

DCC

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

ether

→

expected product

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

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe mixture is left
2. 2
   TemperaturThe reaction mixture is cooled on an ice bath
3. 3
   Sonstigeby 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
   Einengenthe filtrate is concentrated under vacuum
8. 8
   SonstigeThe residue is chromatographed on silica gel
9. 9
   Wascheneluting with a gradient of a DCM/MeOH mixture of from (98/2; v/v) to (96/4; v/v)
10. 10
    SonstigeThe product obtained
11. 11
    Filtrationthe precipitate is spin-filtered off

Vorschrift

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.

Quelle