Реакция #43442

Уравнение реакции

1,1-dimethylethyl {1-[(3-fluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-4-piperidinyl}carbamate

(diethylamino)sulphur trifluoride

sodium bicarbonate

→

product

Выход 33.4%

1,1-Dimethylethyl {1-[((4R/S)-3,4-difluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-4-piperidinyl}carbamate

Выход 33.4%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Другоеthe phases separated
2. 2
   ЭкстракцияThe aqueous phase was extracted twice more with dichloromethane
3. 3
   Другоеevaporated
4. 4
   ПромывкаChromatography eluting with a methanol in dichloromethane gradient

Методика

A solution of 1,1-dimethylethyl {1-[(3-fluoro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-4-piperidinyl}carbamate (15.93 g, 38.1 mmol) in dichloromethane (320 ml) was cooled in an ice bath and treated with (diethylamino)sulphur trifluoride (10.1 ml, 75.9 mmol). After 2.5 hours at room temperature saturated aqueous sodium bicarbonate solution was added, then the phases separated. The aqueous phase was extracted twice more with dichloromethane and the combined organic extracts combined and evaporated. Chromatography eluting with a methanol in dichloromethane gradient afforded the product (5.35 g, 33%).

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