Preparation of optically active enantiomers of piperonyl amines by resolution of the diastereomeric salts

A process for resolving a diastereomeric salt of one of the (S)- or (R)-enantiomers of a compound of Formula (I):

• wherein:
• -L- is a C1-C5 alkylene, carbocyclyl, or heterocyclyl;
• R1 is -alkyl, -benzyl or -phenethyl;
• and
• R2 is -hydrogen, -alkyl, -benzyl or -phenethyl;
• the process comprising:
• forming a diastereomeric salt of the (S)- and (R)-enantiomer of the compound of Formula (I) by mixing the compound of Formula (I) with a chiral acid in a solvent, wherein the diastereomeric salt of one of the (S)- or (R)-enantiomer of the compound of Formula (I) is preferentially crystallized relative to the diastereomeric salt of the other enantiomer of the compound of Formula (I)
• wherein the enantiomeric excess of the compound of Formula (I) is less than about 50%.