Reaktion #40679

Reaktionsgleichung

O-benzyl-N-(t-butoxycarbonyl)-L-serine

triethylamine

ethyl chloroformate

→

t-butyl (1R)-2-(benzyloxy)-1-(hydroxymethyl)ethylcarbamate

Ausbeute 89.2%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe reaction mixture was filtered
2. 2
   workup.ADDITIONone piece of ice was added to the filtrate
3. 3
   workup.ADDITIONSodium borohydride (515 mg) was further added
4. 4
   workup.STIRRINGthe mixture was stirred at room temperature for 6 hrs
5. 5
   workup.ADDITIONThe reaction mixture was diluted with ethyl acetate
6. 6
   Waschenafter washing with water
7. 7
   Trocknenthe organic layer was dried over anhydrous sodium sulfate
8. 8
   SonstigeThe solvent was evaporated
9. 9
   Sonstigethe obtained crude product
10. 10
    Sonstigewas purified by silica gel chromatography (ethyl acetate-hexane)

Vorschrift

O-benzyl-N-(t-butoxycarbonyl)-L-serine (2 g) was dissolved in tetrahydrofuran (20 ml), triethylamine (1.22 ml) was added, and ethyl chloroformate (713 μl) was further added dropwise at 0° C. After stirring the reaction mixture at room temperature for 30 min, the reaction mixture was filtered, and one piece of ice was added to the filtrate. Sodium borohydride (515 mg) was further added, and the mixture was stirred at room temperature for 6 hrs. The reaction mixture was diluted with ethyl acetate and, after washing with water, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane) to give t-butyl (1R)-2-(benzyloxy)-1-(hydroxymethyl)ethylcarbamate (1.7 g)

Quelle