(2S,3S)-2-phenylpiperidin-3-ol → 3-Hydroxy-2-phenylpiperidine

Participants

Reaction Steps

cis-3-Hydroxy-2-phenylpiperidine (Description 3b) and (-)dibenzoyltartrate were dissolved in methanol and crystallized by addition of ethyl acetate. The solid was recrystallised from hot methanol to give the hemi dibenzoyltartrate salt: mp 223°-224° C. This was liberated from the salt as described above to give the single enantiomer (+)-cis-3-hydroxy-2-phenylpiperidine, mp 93°-95° C. [a]23D =+98.5° (c=1, MeOH). The mother liquors were converted to the free base as described in Description 3b and crystallization using (+)dibenzoyltartrate in an analogous manner to that described above gave (-)-3-hydroxy-2-phenylpiperidine, mp 93°-95° C. [a]23D =-97.2° (c=1, MeOH).

Provenance & Evidence