Aluminium lithium hydride → (2R,3R)-1-(Benzylamino)butane-2,3-diol

Temperature

0 °C

A flask was charged with 3.03 g (14.5 mmol) (2S,3R)-N-benzyl-2,3-dihydroxy-butyramide, 60 mL dry THF, and the mixture was cooled to 0° C. under a nitrogen atmosphere. To this solution, 1.65 g (43.5 mmol) lithium aluminum hydride powder was added in small portions. The mixture was stirred at 0° C. for 1 hour, allowed to warm to room temperature, and then heated at reflux overnight. The reaction mixture was then cooled to 0° C. and quenched by the slow addition of 1.65 mL water, 1.65 mL 15% aqueous sodium hydroxide solution, and 4.95 mL water, sequentially. The solids were filtered off, and the solvent was removed under reduced pressure. The crude material was purified by column chromatography (1:1 dichloromethane/ methanol) to give 1.41 g (50%) of the title compound as a white solid. MS (APCI) (m+1)/z 196.1.

1. temperatureto warm to room temperature
2. temperatureheated
3. temperatureat reflux overnight
4. temperatureThe reaction mixture was then cooled to 0° C.
5. customquenched by the slow addition of 1.65 mL water, 1.65 mL 15% aqueous sodium hydroxide solution, and 4.95 mL water
6. filtrationThe solids were filtered off
7. customthe solvent was removed under reduced pressure
8. customThe crude material was purified by column chromatography (1:1 dichloromethane/ methanol)

ORD record

ord-399a633a84e44a6197ea451eda6352bd

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07196090B2