Reaktion #1122642

Reaktionsgleichung

5-(trifluoromethyl)pyridin-3-amine

N-methylpyrrolidine

EtOAc

isopropenyl chloroformate

→

prop-1-en-2-yl 5-(trifluoromethyl)pyridin-3-ylcarbamate

Lösungsmittel

CH2Cl2

H2O

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give a brown suspension
2. 2
   Sonstigeto reach RT
3. 3
   Sonstigethe organic layer was isolated
4. 4
   Waschenwashed with 50% brine (10 mL)
5. 5
   Trocknendried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   Sonstigeto leave a brown oil, which
9. 9
   Sonstigepurified by column chromatography on silica gel
10. 10
    Wascheneluting with EtOAc in CH2Cl2 (6%→40%)
11. 11
    Sonstigeto give a white solid

Vorschrift

5-(trifluoromethyl)pyridin-3-amine (883 mg, 5.45 mmol) was suspended in dry THF (20 mL) and N-methylpyrrolidine (680 μL, 6.54 mmol) was added to give a brown suspension. The mixture was cooled to 0° C. and isopropenyl chloroformate (715 μL, 6.54 mmol) was added dropwise over 15 min. The suspension was allowed to reach RT and was stirred for 4 h. EtOAc (60 mL) and H2O (10 mL) were added and the organic layer was isolated, washed with 50% brine (10 mL), dried (MgSO4), filtered and evaporated to leave a brown oil, which solidified upon standing (1.05 g). The solid was taken up in CH2Cl2 (4 mL) and purified by column chromatography on silica gel, eluting with EtOAc in CH2Cl2 (6%→40%), to give a white solid. Yield: 600 mg (45%).

Quelle