1-Phenethylamine, (+)- → HCID 54194683, compound

HRID 2226566Notes

Reaction equation

HRID 2226566 reaction equation
C[C@@H](N)C1C=CC=CC=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:14][C:15]1([CH3:22])[NH:19][C:18](=[O:20])[NH:17][C:16]1=[O:21]>CC(C)=O>[Cl:10][C:11]1[CH:12]=[C:13]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:14][C@:15]1([CH3:22])[NH:19][C:18](=[O:20])[NH:17][C:16]1=[O:21]

Participants

4

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 23297209HCID 23297209, compound

Product 1

HCID 54194683HCID 54194683, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Advantageously, compared to this preparation which comprises six steps in all, the preferred process for the purposes of the invention, which is faster and more economical, enables (S)-(-)-2-amino-2-(3,4-dichlorobenzyl)-1-propanol to be prepared in four synthesis steps from 3,4-dichlorophenylacetone. Essentially, the process consists in reacting the ketone by the Bucherer-Berg reaction with potassium cyanide and ammonium carbonate to obtain (+/-)-5-(3,4-dichlorobenzyl)-5-methylhydantoin, which is subjected in an alkaline aqueous-acetone medium to a stereospecific salification with (R)-(+)-α-methylbenzylamine so as to obtain the addition salt thereof with the (S)-(-) enantiomer of the hydantoin, which, being insoluble, is filtered off, and from which (S)-(-)-5-(3,4-dichlorobenzyl)-5-methylhydantoin is obtained in a state of optical purity greater than 98% by treatment in an acid solution.

Workup

  1. customto obtain the addition salt
  2. filtrationis filtered off

Sources & evidence

ORD record
ord-ceff27b35b90411188ee675f0f0a5858
Source dataset
uspto-grants-1994_09
Patent number
US05348980

Reaction notes

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