Реакция #52237

Уравнение реакции

Triethylamine

Oxalyl chloride

Dimethyl sulfoxide

1-Boc-piperidine-4-methanol

→

1-Boc-piperidine-4-carboxaldehyde

Выход 91.0%

Растворители

water

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe mixture stirred for 1 h
2. 2
   workup.STIRRINGthe mixture stirred at −78° C. for 30 min
3. 3
   Температураwarmed to room temperature over the course of 1 h
4. 4
   Другоеthe layers separated
5. 5
   ЭкстракцияThe water layer was extracted with dichloromethane
6. 6
   Сушкаdried (Na2SO4)
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated

Методика

Dimethyl sulfoxide (3.5 mL, 48.7 mmol) was dissolved in dichloromethane (100 mL) and was cooled to −78° C. Oxalyl chloride (3.65 mL, 41.8 mmol) was added. The mixture stirred for 30 min. To this solution was added a solution of 1-Boc-piperidine-4-methanol (7.5 g, 34.8 mmol) in dichloromethane (15 mL), and the mixture stirred for 1 h. Triethylamine (9.7 mL, 69.6 mmol) was added slowly and the mixture stirred at −78° C. for 30 min and warmed to room temperature over the course of 1 h. The mixture was diluted with water and the layers separated. The water layer was extracted with dichloromethane and the organic layers combined, dried (Na2SO4), filtered and concentrated to provide 1-Boc-piperidine-4-carboxaldehyde (6.75 g, 91%) as a yellow oil.

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