Tetrahydrofuran → 4-Benzyloxycarbonylamino-4-hydroxymethyl piperidine-1-carboxylic acid tert-butyl ester

Temperatur

-15 °C

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.

1. additionwas added at room temperature
2. stirringthe mixture was stirred at room temperature for 1 hour
3. waitstood still overnight
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with ethyl acetate
6. washthe resultant solution was washed with water
7. dry with materialan aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
8. customthe solvent was removed under reduced pressure

ORD-Eintrag

ord-46a257f0bf9141ecbb1657d9630fbdf0

Quelldatensatz

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08524738B2