تفاعل #8862

معادلة التفاعل

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

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted three times with ethyl acetate
2. 2
   غسيلThe combined organic layers were washed with brine
3. 3
   تجفيفdried over sodium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated
6. 6
   workup.ADDITIONa mixture of bromide starting material and title product

الإجراء التجريبي

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.

المصدر