tert-Butyl 3-acetoxyazetidine-1-carboxylate

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tert-Butyl 3-acetoxyazetidine-1-carboxylate Basic information
Product Name:tert-Butyl 3-acetoxyazetidine-1-carboxylate
Synonyms:tert-Butyl 3-acetoxyazetidine-1-carboxylate;1-Azetidinecarboxylic acid, 3-(acetyloxy)-, 1,1-dimethylethyl ester
CAS:1215205-53-0
MF:C10H17NO4
MW:215.25
EINECS:
Product Categories:
Mol File:1215205-53-0.mol
tert-Butyl 3-acetoxyazetidine-1-carboxylate Structure
tert-Butyl 3-acetoxyazetidine-1-carboxylate Chemical Properties
Boiling point 269.0±33.0 °C(Predicted)
density 1.13±0.1 g/cm3(Predicted)
storage temp. 2-8°C
pka-3.28±0.40(Predicted)
Safety Information
MSDS Information
tert-Butyl 3-acetoxyazetidine-1-carboxylate Usage And Synthesis
Synthesis
Acetic anhydride

108-24-7

1-N-Boc-3-hydroxyazetidine

141699-55-0

tert-Butyl 3-acetoxyazetidine-1-carboxylate

1215205-53-0

General procedure for the synthesis of tert-butyl 3-acetoxyazetidine-1-carboxylate from ethanoic anhydride and N-Boc-3-hydroxyazetidine: 0.27 g (1.559 mmol) of N-Boc-3-hydroxyazetidine, 0.61 g (4.677 mmol) of diisopropylethylamine and a catalytic amount of 4-dimethylaminopyridine were dissolved at 0 °C in 7 mL of dichloromethane in dichloromethane. To this solution 0.32 g (2 mmol) of acetic anhydride was slowly added, followed by stirring the reaction for 16 hours at room temperature. After completion of the reaction, the solvent was removed by vacuum distillation. The crude product was purified by column chromatography using a mixed solvent system of hexane and ethyl acetate (3:1, v/v) to give 0.33 g (98% yield) of tert-butyl 3-acetoxyazetidine-1-carboxylate. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 5.12 (1H, m), 4.23 (2H, dd), 4.12 (2H, dd), 2.09 (3H, s), 1.44 (9H, s).

References[1] Patent: US2011/166121, 2011, A1. Location in patent: Page/Page column 56
tert-Butyl 3-acetoxyazetidine-1-carboxylate Preparation Products And Raw materials
Raw materialsAcetic anhydride-->Dichloromethane-->N,N-Diisopropylethylamine-->1-N-Boc-3-hydroxyazetidine-->4-Dimethylaminopyridine
Tag:tert-Butyl 3-acetoxyazetidine-1-carboxylate(1215205-53-0) Related Product Information
1-N-Boc-3-hydroxyazetidine 1-Boc-3-(methoxy)azetidine N-Boc-3-(prop-2-yn-1-yloxy)azetidine Azetidin-3-ylacetate Methyl3-hydroxyazetidine-1-carboxylate Benzyl 3-acetoxyazetidine-1-carboxylate