4-Methylmorpholine → (1S)-[1-Hydroxymethyl-3-(tritylcarbamoyl)propyl]carbamic Acid Benzyl Ester

Temperatur

23 °C

4-Methylmorpholine (1.89 mL, 17.2 mmol, 1 equiv) and ethyl chloroformate (1.65 mL, 17.3 mmol, 1 equiv) were added to a mixture of commercially available Cbz-Gln(Trt)-OH (9.00 g, 17.2 mmol, 1 equiv) in THF (23 mL) at −10° C. After stirring 20 min, the reaction mixture was filtered and the filtrate was added dropwise to a suspension of NaBH4 (1.47 g, 38.9 mmol, 2.25 equiv) in H2O (10 mL) at 0° C. The resulting mixture was allowed to warm to 23° C. and stirred for 5 h. It was then cooled again to 0° C., quenched by the careful addition of 1 N HCl (30 mL) and then partitioned between MTBE (500 mL) and brine (2×100 mL). The organic phase was dried over Na2SO4 and evaporated to provide the title intermediate which was used without further purification.

1. filtrationthe reaction mixture was filtered
2. stirringstirred for 5 h
3. temperatureIt was then cooled again to 0° C.
4. customquenched by the careful addition of 1 N HCl (30 mL)
5. custompartitioned between MTBE (500 mL) and brine (2×100 mL)
6. dry with materialThe organic phase was dried over Na2SO4
7. customevaporated

ORD-Eintrag

ord-922dbb5c2c104c169669214862f2bb92

Quelldatensatz

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06514997B2