Triethylamine → Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylate

Temperature

0 °C

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-while solid (2.2 g, 36% yield); ES-MS: 252.08 (M+H).

1. additionAfter addition
2. temperaturethe reaction mixture was warmed to RT
3. customwas completely consumed
4. filtrationThe reaction mixture was filtered
5. additionCH2Cl2 was added to the filtrate (100 mL)
6. washThe organics were washed with water (2×30 mL), brine solution (30 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customto obtain crude product, which
11. customwas purified by silica gel chromatography (5% EtOAc/hexanes

ORD record

ord-283275612010450a84f46a0a87ecec71

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232406B2