Reaktion #7382

Reaktionsgleichung

[((benzyloxy)carbonyl]amino}pentanedioate

lithium borohydride

→

title compound

Ausbeute 81.2%

Benzyl (1R)-4-hydroxy-1-(hydroxymethyl)butylcarbamate

Ausbeute 81.2%

Lösungsmittel

THF

THF

brine

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   WaschenThe combined organic extracts were washed with brine
3. 3
   Trocknendried (over magnesium sulphate)
4. 4
   Einengenconcentrated under reduced pressure

Vorschrift

A solution of dimethyl (2R)-2-{[((benzyloxy)carbonyl]amino}pentanedioate (22.4 g) in dry THF (74 ml) was added dropwise over 1 h to a stirred mixture of lithium borohydride (4.5 g) in THF (200 ml) at room temperature, under nitrogen. Stirring at room temperature was continued for 3 days. The reaction mixture was diluted with brine and water, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (over magnesium sulphate) and concentrated under reduced pressure to give the title compound (16.5 g) as a white solid.

Quelle