Reacción #67977

Ecuación de reacción

sodium borohydride

tetrahydrofuran

4-(((benzyloxy)carbonyl)amino)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid

ethyl chlorocarbonate

→

tert-butyl 4-(((benzyloxy)carbonyl)amino)-4-(hydroxymethyl)piperidine-1-carboxylate

Disolventes

water

ethyl acetate

water

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 1 hour
3. 3
   workup.WAITstood still overnight
4. 4
   OtroThe organic layer was separated
5. 5
   Extracciónthe aqueous layer was extracted with ethyl acetate
6. 6
   Lavadothe resultant solution was washed with water
7. 7
   Secadoan aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
8. 8
   Otrothe solvent was removed under reduced pressure

Procedimiento

To 20 mL of a tetrahydrofuran suspension containing 1.0 g of 4-(((benzyloxy)carbonyl)amino)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid, 0.41 mL of triethylamine was added at room temperature, then the mixture cooled to −15° C., and thereto was added dropwise 0.28 mL of ethyl chlorocarbonate. The reaction mixture was stirred at 5 to 10° C. for 1 hour. Thereto were added 0.11 g of sodium borohydride and 3 mL of water, and the mixture was stirred at room temperature for 1 hour, and stood still overnight. The reaction mixture was added with ethyl acetate and water. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, and the resultant solution was washed with water and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.55 g of a colorless oily substance, tert-butyl 4-(((benzyloxy)carbonyl)amino)-4-(hydroxymethyl)piperidine-1-carboxylate.

Fuente