Reaktion #92567

Reaktionsgleichung

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

DCC

Et3N

N,O-dimethylhydroxylamine hydrochloride

→

crude product

Ausbeute 127.9%

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

Ausbeute 127.9%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenConcentrated under reduced pressure
2. 2
   Sonstigeto remove solvent
3. 3
   Extraktionthe aqueous was further extracted with EA (50 mL×3)
4. 4
   WaschenThe combined organic phases were washed with brine (20 mL)
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   Sonstigeto remove solvent
7. 7
   Sonstigepurified by column chromatography on silica gel (200-300 mesh, CH2Cl2/MeOH=20/1)

Vorschrift

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.

Quelle