Resolution of racemic 12-hydroxyl-1,15-pentadecanlactam using d-glucose derivative as a chiral auxiliary

Racemic 12-hydroxyl-1,15-pentadecanlactam 2 was resolved using glucose as a chiral auxiliary for the first time. Both the (R)- and (S)-isomers were obtained in high enantiomeric excesses (>99% by HPLC). The absolute configuration of (+)-2b and (−)-2a was determined by Horeau’s method and a modified Mosher’s method.

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(S)-12-Hydroxyl-1,15-pentadecanlactamC15H29NO2Ee >99%[α]D20=+10.03 (c 0.46, CHCl3)Source of chirality: chiral resolutionConfiguration: (S)