Reacción #46383

ord-10a904a3eba64466bb5d478119d5fb0d

Ecuación de reacción

CC(C)(C)OC(=O)N1CCC[C@H]1CN
(S)-2-Aminomethylpyrrolidine-1-carboxylic acid tert-butyl ester
N#Cc1ccc(Cl)nc1
6-chloronicotinonitrile
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCN(C(C)C)C(C)C
diisopropylethylamine
CC(C)(C)OC(=O)N1CCC[C@H]1CNc1ccc(C#N)cn1
title compound
Rendimiento 44.2%
CC(C)(C)OC(=O)N1CCC[C@H]1CNc1ccc(C#N)cn1
(S)-2-[(5-Cyano-pyridin-2-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
Rendimiento 44.2%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturacooled
  2. 2
    Filtraciónthe mixture filtered through kieselguhr
  3. 3
    OtroThe filtrate was evaporated
  4. 4
    Otrothe residue chromatographed on silica gel
  5. 5
    Lavadoeluting with ethyl acetate-hexane mixtures

Procedimiento

(S)-2-Aminomethylpyrrolidine-1-carboxylic acid tert-butyl ester (0.3 g), 6-chloronicotinonitrile (0.21 g), potassium carbonate (0.41 g) and diisopropylethylamine (0.78 ml) were heated in xylene at 130° C. for 26 h, cooled and the mixture filtered through kieselguhr. The filtrate was evaporated and the residue chromatographed on silica gel, eluting with ethyl acetate-hexane mixtures to afford the title compound (0.2 g). Mass Spectrum (API+): Found 303 (MH+). C16H22N4O2 requires 302.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07741329B2uspto-grants-2010_06