Réaction #341177

Équation de réaction

methanesulfonyl chloride

tert-butyl 3-hydroxyazetidine-1-carboxylate

Et3N

→

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

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter addition
2. 2
   Températurethe reaction mixture was warmed to RT
3. 3
   Autrewas completely consumed
4. 4
   FiltrationThe reaction mixture was filtered
5. 5
   workup.ADDITIONCH2Cl2 was added to the filtrate (100 mL)
6. 6
   LavageThe organics were washed with water (2×30 mL), brine solution (30 mL)
7. 7
   Séchagedried (Na2SO4)
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated
10. 10
    Autreto obtain crude product, which
11. 11
    Autrewas purified by silica gel chromatography (5% EtOAc/hexanes

Mode opératoire

To a solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (6.0 g, 34.68 mmol) in DCM was added by Et3N. The mixture was cooled to 0° C. and methanesulfonyl chloride was slowly added. After addition was complete, the reaction mixture was warmed to RT and stirred until starting material was completely consumed as indicated by TLC (40% EtOAc/hexanes). The reaction mixture was filtered and CH2Cl2 was added to the filtrate (100 mL). The organics were washed with water (2×30 mL), brine solution (30 mL), dried (Na2SO4), filtered, and concentrated to obtain crude product, which was purified by silica gel chromatography (5% EtOAc/hexanes, then 15% EtOAc/hexanes). 1-(tert-Butoxycarbonyl)azetidin-3-yl methanesulfonate was isolated as an off-white solid (2.2 g, 36% yield); ES-MS: 252.08 (M+H).

Source