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

HRID 863773Notes

Reaction equation

HRID 863773 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][NH:4][C@H:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO>[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 1

HCID 11008479(2S,3S)-2-phenylpiperidin-3-ol

Product 1

HCID 187826433-Hydroxy-2-phenylpiperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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. [α]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. [α]23D =-97.2° C. (c=1, MeOH).

Workup

  1. customas described in Description 3b and crystallization

Sources & evidence

ORD record
ord-58b017bcb7b1481e99089e30b3985453
Source dataset
uspto-grants-1996_10
Patent number
US05561130

Reaction notes

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