HCID 131729327, compound → HCID 67533258, compound

HRID 658229Notes

Reaction equation

HRID 658229 reaction equation
[Cl:1][C:2]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([Cl:37])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][C@H:15]2[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:10][CH:9]=1>CCO>[Cl:1][C:2]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([Cl:37])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C@H:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][C@@H:15]2[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:12][CH:13]=1

Participants

3

Reactant 1

HCID 131729327HCID 131729327, compound

Product 1

HCID 67533258HCID 67533258, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Racemic trans-1-tert-butyl 3-ethyl 4-{4-[2-(2,6-dichloro-4-methylphenoxy)-ethoxy]phenyl}-piperidine-1,3-dicarboxylate was resolved by a Chiral Pak AD preparative column (15% EtOH in Hex) to afford two enantiomers. 1-tert-Butyl 3-ethyl (3R,4S)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-phenyl}piperidine-1,3-dicarboxylate was eluted as the slower enantiomer (retention time=26.5 min).

Workup

  1. customto afford two enantiomers
  2. wash1-tert-Butyl 3-ethyl (3R,4S)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-phenyl}piperidine-1,3-dicarboxylate was eluted as the slower enantiomer (retention time=26.5 min)

Sources & evidence

ORD record
ord-ce2ff6d424ba4d7e85c9f42956f39446
Source dataset
uspto-grants-2011_12
Patent number
US08076359B2

Reaction notes

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