HCID 57496385, compound → HCID 57496421, compound

HRID 537739Notes

Reaction equation

HRID 537739 reaction equation
[CH:1]1([CH:7]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:10][CH2:9][N:8]2C(OCC2C=CC=CC=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCO.[Pd]>[CH:1]1([C@@H:7]2[CH2:12][C@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:10][CH2:9][NH:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 57496385HCID 57496385, compound

Product 1

HCID 57496421HCID 57496421, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl 2-cyclohexyl-4-phenylpiperidine-1-carboxylate (1.05 g, 2.78 mmol) in EtOH (50 ml) was added Pd/C (0.5 g, 0.235 mmol) and hydrogenated with a balloon overnight. Filtered through celite and concentrated. The trans isomer was removed on the chiral OD column 20% IPA/Hexanes w/DEA affording the single cis diastereomer.

Workup

  1. customhydrogenated with a balloon overnight
  2. filtrationFiltered through celite
  3. concentrationconcentrated
  4. customThe trans isomer was removed on the chiral OD column 20% IPA/Hexanes
  5. customw/DEA affording the single cis diastereomer

Sources & evidence

ORD record
ord-4310c8dc9c3a4f1682a3a0a664705109
Source dataset
uspto-grants-2014_10
Patent number
US08865701B2

Reaction notes

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