Enantioselective Biocatalytic Preparation of 4-Cyano-Substituted 1-Aminoindane and Ozanimod

A process for the enantioselective biocatalytic preparation of 4-substituted 1-aminoindanes of general formula (S)-I:

• wherein
• R is selected from the group consisting of halogen;
• —CN;
• —C(═O)H;
• —C(═N—OH)H;
• —C(═O)NH2;
• —C(═O)OH;
• —C(═NH)NH—OH;
• —C(═N—OH)NH2;
• and —COOR1, wherein R1 is selected from the group consisting of H;
• C1 to C8-alkyl;
• arylalkyl, wherein alkyl is C1 to C8-alkyl;
• —CH2-Hal, wherein Hal is F, Cl or Br;
• —CH2—O-alkyl, wherein alkyl is C1 to C8-alkyl;
• optionally substituted aryl;
• and optionally substituted heteroaryl;
• Y is selected from the group consisting of H;
• —C(═O)R1y;
• and —C(═O)OR1y, wherein R1y is selected from the group consisting of H;
• C1 to C8-alkyl;
• arylalkyl, wherein alkyl is C1 to C8-alkyl;
• —CH2-Hal, wherein Hal is F, Cl or Br;
• —CH2—O-alkyl, wherein alkyl is C1 to C8-alkyl;
• optionally substituted aryl;
• and optionally substituted heteroaryl;
• via resolution of a racemic or enantiomerically-enriched amine mixture of 4-substituted indan-1-amine compounds of general formulae (S)-II and (R)-II
• wherein R is as defined above via an enantioselective acylation in the presence of a lipase.