Reacción #8862

Ecuación de reacción

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

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted three times with ethyl acetate
2. 2
   LavadoThe combined organic layers were washed with brine
3. 3
   Secadodried over sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated
6. 6
   workup.ADDITIONa mixture of bromide starting material and title product

Procedimiento

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.

Fuente