(-)-Epichlorohydrin → Epichlorohydrin

Participants

Reaction Steps

Following the method outlined above for (R/S)-4-[3-(4-butylpiperidin-1-yl)-2-hydroxypropyl]-4H-benzo[1,4]oxazin-3-one using (R)-(−)-epichlorohydrine (97% ee), (instead of racemic epichlorohydrin, gave the title compound. The optical purity was determined by HPLC analysis (Chiralpak AD, 250×4.6, 5 μm; hexane/i-PrOH/diethylamine 95:4.7:0.3, 0.5 mL/min) to be 96.3% ee. ([α]D20=−6, c=0.5, EtOH). 1H NMR, 13C NMR and HPLC-MS spectral data were identical to those of the racemic compound.

Provenance & Evidence