Реакция #8862

Уравнение реакции

sodium bicarbonate

KHMDS

tert-butyl 4-methoxycarbonylpiperidine-1-carboxylate

2-bromo-1-(tert-butyldimethylsilyloxy)ethane

→

tert-Butyl 4-methoxycarbonyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Экстракцияextracted three times with ethyl acetate
2. 2
   ПромывкаThe combined organic layers were washed with brine
3. 3
   Сушкаdried over sodium sulfate
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated
6. 6
   workup.ADDITIONa mixture of bromide starting material and title product

Методика

To a solution of KHMDS (8.72 g, 44 mmol) in THF (300 mL) at −70° C. was slowly added over 10 min a solution of tert-butyl 4-methoxycarbonylpiperidine-1-carboxylate (7.1 g, 29 mmol) in THF (70 mL). After 1 h, 2-bromo-1-(tert-butyldimethylsilyloxy)ethane (10 g, 47 mmol) was added and the reaction was allowed to warm to room temperature for 1 h. The mixture was poured into aq. sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was used directly in the next step. TLC (50% ethyl acetate in hexanes) indicated a mixture of bromide starting material and title product.

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