Reaktion #159304

Reaktionsgleichung

(R)-tert-butyl 3-aminopyrrolidine-1-carboxylate

2-fluoro-5-cyanopyridine

i-Pr2NEt

n-PrOH

→

(R)-tert-butyl 3-(5-cyanopyridin-2-ylamino)pyrrolidine-1-carboxylate

Ausbeute 89.6%

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA heavy-walled, screw-cap glass tube
2. 2
   Waschenwashed with 1% aq HCl (3×40 mL)
3. 3
   Trocknendried over Na2SO4
4. 4
   SonstigeRemoval of the solvent
5. 5
   workup.WAITleft an oil (3.28 g) which
6. 6
   Sonstigewas purified by chromatography on a 40-g silica gel cartridge
7. 7
   Wascheneluted with a 0-100% EtOAc in hexanes gradient

Vorschrift

A heavy-walled, screw-cap glass tube was charged with (R)-tert-butyl 3-aminopyrrolidine-1-carboxylate (3.30 g, 17.7 mmol), 2-fluoro-5-cyanopyridine (1.63 g, 13.2 mmol), i-Pr2NEt (6.3 mL, 35.5 mmol) and n-PrOH (3 mL). The mixture was heated at 150° C. in an oil bath for 2 h. The mixture was diluted with EtOAc (180 mL), washed with 1% aq HCl (3×40 mL), satd aq NaHCO3 (40 mL) and brine (40 mL), and dried over Na2SO4. Removal of the solvent left an oil (3.28 g) which was purified by chromatography on a 40-g silica gel cartridge eluted with a 0-100% EtOAc in hexanes gradient to afford (R)-tert-butyl 3-(5-cyanopyridin-2-ylamino)pyrrolidine-1-carboxylate (3.41 g, 88% based on 2-fluoro-5-cyanopyridine). LC-MS Method 1 tR=1.57 min, m/z=289.

Quelle