Réaction #92567

Équation de réaction

1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid

DCC

Et3N

N,O-dimethylhydroxylamine hydrochloride

→

crude product

Rendement 127.9%

Tert-butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate

Rendement 127.9%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   ConcentrationConcentrated under reduced pressure
2. 2
   Autreto remove solvent
3. 3
   Extractionthe aqueous was further extracted with EA (50 mL×3)
4. 4
   LavageThe combined organic phases were washed with brine (20 mL)
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   Autreto remove solvent
7. 7
   Autrepurified by column chromatography on silica gel (200-300 mesh, CH2Cl2/MeOH=20/1)

Mode opératoire

To a solution of 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (5.15 g, 25.6 mmol) in THF (100 mL) was added DCC (7.11 g, 34.5 mmol), Et3N (5.18 g, 51.2 mmol) and N,O-dimethylhydroxylamine hydrochloride (3.44 g, 35.3 mmol), the reaction was stirred at RT for about 16 hr. Concentrated under reduced pressure to remove solvent, the residue was portioned between EA (100 mL) and water (50 mL), the aqueous was further extracted with EA (50 mL×3). The combined organic phases were washed with brine (20 mL), concentrated under reduced pressure to remove solvent, then purified by column chromatography on silica gel (200-300 mesh, CH2Cl2/MeOH=20/1) to give the crude product (˜8.0 g) as a colorless oil. MS (ESI) m/e [M+23]+ 266.9, [M−55]+ 189.0.

Source