4-Toluenesulfonyl chloride → 3-Hydroxy-4-tosyloxybutanenitrile

Participants

Reaction Steps

tosylating 3,4-dihydroxybutanenitrile by reacting 3,4-dihydroxybutanenitrile with dibutyltinoxide, p-toluene sulphonyl chloride and a base in the presence of an organic solvent, at a temperature ranging between 25-30° C. under nitrogen atmosphere, for a period of 1-3 hrs., adding water to the above said reaction mixture and separating the organic layer, followed by concentration and purification by known method to obtain the racemic 3-hydroxy-4-tosyloxybutanenitrile, ii) resoluting racemic 3-hydroxy-4-tosyloxybutanenitrile with an acetylating agent in the presence of lipase in an organic solvent, at a temperature of 25-30° C. followed by filtration and washing to obtain (R)-3-hydroxy-4-tosyloxybutanenitrile, iii) converting (R)-3-hydroxy-4-tosyloxybutanenitrile (R)-GABOB and (R)-carnitine by reacting it with a base in an organic solvent under reflux for an overnight period followed by evaporation, adding concentrated HCl to the resultant residue and heating to a temperature in the range of 60-90° C., for a period of about 6 hr followed by evaporation and purification by known method to obtain the desired product.

Provenance & Evidence