N-[1-(4-Chlorophenyl)ethyl]-2-methoxyacetamide → (1R)-1-(4-chlorophenyl)ethan-1-amine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10]C(=O)COC)[CH3:9])=[CH:4][CH:3]=1.P([O-])(O)(O)=O.[Na+].P([O-])(O)(O)=O.[Na+].[Na+].P([O-])(O)(O)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 40 °C
Procedure
A mixture of 200 mg (0.88 mmol) of racemic N-[1-(4-chloro-phenyl)-ethyl]-methoxy-acetamide and 50 U of Candida antarctica lipase (Novozym 435®) was made up to a volume of 7 ml using a 50 mM aqueous solution of sodium dihydrogen phosphate/disodium dihydrogen phosphate buffer mixture. The reaction mixture, which had a pH value of 8, was shaken at 40° C. for 48 hours. The reaction mixture was then extracted three times with di-isopropyl-ether. The combined organic phases were concentrated under reduced pressure. The remaining residue was gas-chromatographically analysed by means of a chiral column. By these means, it was found that the reaction had proceeded with a conversion rate of 48%. The (R)-1-(4-chloro-phenyl)-ethyl-amine formed showed an ee value of 99%.
Workup
- extractionThe reaction mixture was then extracted three times with di-isopropyl-ether
- concentrationThe combined organic phases were concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-42b62fb0da434333ae3f0361ae289881
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05885787
Reaction notes
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