반응 #8862

반응 방정식

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

용매

THF

THF

반응 조건

후처리

1. 1
   추출extracted three times with ethyl acetate
2. 2
   세척The combined organic layers were washed with brine
3. 3
   건조dried over sodium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated
6. 6
   workup.ADDITIONa mixture of bromide starting material and title product

실험 절차

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.

출처