4-Toluenesulfonyl chloride → 3-Hydroxy-4-tosyloxybutanenitrile
Reaction equation
[OH:1][CH:2]([CH2:6][OH:7])[CH2:3][C:4]#[N:5].C([Sn](=O)CCCC)CCC.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>O>[OH:1][CH:2]([CH2:6][O:7][S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25])[CH2:3][C:4]#[N:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- customto the above said reaction mixture
- customseparating the organic layer
- concentrationfollowed by concentration and purification by known method
Sources & evidence
- ORD record
- ord-a5dfb54ec6934ad5b7c7af10ae73bcfd
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816119B2
Reaction notes
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