Réaction #341178

Équation de réaction

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

4-iodopyrazole

NaH

→

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

Rendement 62.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Températureheated 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
   Autreresulting precipitate
5. 5
   Filtrationcollected by filtration
6. 6
   Autredried
7. 7
   LavageThe resulting residue washed with pentane
8. 8
   Autredried

Mode opératoire

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).

Source