تفاعل #92567

معادلة التفاعل

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

DCC

Et3N

N,O-dimethylhydroxylamine hydrochloride

→

crude product

المردود 127.9%

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

المردود 127.9%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   تركيزConcentrated under reduced pressure
2. 2
   أخرىto remove solvent
3. 3
   استخلاصthe aqueous was further extracted with EA (50 mL×3)
4. 4
   غسيلThe combined organic phases were washed with brine (20 mL)
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   أخرىto remove solvent
7. 7
   أخرىpurified by column chromatography on silica gel (200-300 mesh, CH2Cl2/MeOH=20/1)

الإجراء التجريبي

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.

المصدر