Reaktion #341178

Reaktionsgleichung

1-(tert-butoxycarbonyl)azetidin-3-yl methanesulfonate

4-iodopyrazole

NaH

→

tert-butyl 3-(4-iodo-1H-pyrazol-1-yl)azetidine-1-carboxylate

Ausbeute 62.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated at 100° C. for 5 hours
2. 2
   workup.ADDITIONThe reaction mixture was poured into ice cold water
3. 3
   workup.STIRRINGstirred for 30 minutes
4. 4
   Sonstigeresulting precipitate
5. 5
   Filtrationcollected by filtration
6. 6
   Sonstigedried
7. 7
   WaschenThe resulting residue washed with pentane
8. 8
   Sonstigedried

Vorschrift

At 0° C., a solution of 4-iodopyrazole (3.0 g, 15.46 mmol) in DMF (40 mL) was treated with NaH (60% mineral oil dispersion, 1.11 g, 46.39 mmol) in portions. The mixture stirred for 30 minutes, followed by the slow addition of 1-(tert-butoxycarbonyl)azetidin-3-yl methanesulfonate (5.0 g, 20.1 mmol). The reaction mixture was warmed to RT and then heated at 100° C. for 5 hours. The reaction mixture was poured into ice cold water, stirred for 30 minutes, and resulting precipitate collected by filtration and dried. The resulting residue washed with pentane and dried to obtain tert-butyl 3-(4-iodo-1H-pyrazol-1-yl)azetidine-1-carboxylate (3.3 g, 62% yield); 1H-NMR (400 MHz, CDCl3): 7.58 (s, 1H), 7.57 (s, 1H), 5.07-5.0 (m, 1H), 4.39-4.34 (m, 2H), 4.29-4.25 (dd, 2H), 1.45 (s, 9H).

Quelle