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

HRID 1377942Notes

Reaction equation

HRID 1377942 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 1 (d)) 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 3 b and crystallization using (+)dibenzoyltartrate in an analogous manner to that described above gave the product, mp 93°-95° C. [a]23D =-97.2° C. (c=1, MeOH).

Workup

  1. customas described in Description 3 b and crystallization
  2. customabove gave the product, mp 93°-95° C. [a]23D =-97.2° C. (c=1, MeOH)

Sources & evidence

ORD record
ord-d0ec3a2b6dea4f2c8018c7578fe36101
Source dataset
uspto-grants-1997_09
Patent number
US05665883

Reaction notes

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