Reaction #7382

Reaction equation

[((benzyloxy)carbonyl]amino}pentanedioate

lithium borohydride

→

title compound

Yield 81.2%

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

Yield 81.2%

Solvents

THF

THF

brine

water

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe combined organic extracts were washed with brine
3. 3
   Dryingdried (over magnesium sulphate)
4. 4
   Concentrationconcentrated under reduced pressure

Procedure

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.

Source