Aluminium lithium hydride → HCID 68887617, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of LAH (0.6 g) in THF (40 ml) is added at 0° C. a solution of ((1S,2R)-1-Benzyl-3-cyano-2-hydroxy-propyl)-carbamic acid tert-butyl ester (1.1 g) in THF (15 ml). The mixture is stirred for 1 h at 0° C. and then quenched with water and 3N aqueous sodium hydroxide. After filtration the solution is concentrated under reduced pressure and purified by preparative HPLC (gradient of water, 0.1% TFA/acetonitrile, 0.1% TFA from 80/20 to 0/100 on Nucleosil 100-10 C18 column). The fractions containing ((1S,2R)-4-Amino-1-benzyl-2-hydroxy-butyl)-carbamic acid tert-butyl ester are set to a basic pH by addition of soda and extracted with EtOAc. The organic layer is dried over sodium sulfate and concentrated under reduced pressure to give 682 mg of the desired product.

Provenance & Evidence