Ammonium formate → (S)-6-Cyclohexyl-piperidin-2-one

HRID 579182Notes

Reaction equation

HRID 579182 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][C@@H:8]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[NH:9][C@H](C1C=CC=CC=1)C)C.C([O-])=O.[NH4+]>CO.[Pd]>[CH:18]1([C@H:8]2[NH:9][C:4](=[O:3])[CH2:5][CH2:6][CH2:7]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66684789(S)-5-Cyclohexyl-5-((S)-1-phenyl-ethylamino)-pentanoic acid ethyl ester

Product 1

HCID 66684732(S)-6-Cyclohexyl-piperidin-2-oneYield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-5-Cyclohexyl-5-((S)-1-phenyl-ethylamino)-pentanoic acid ethyl ester (2.0 g, 6.0 mmol, 1.0 equiv) in MeOH (60 mL) was added Pd (1.6 g, 10% on carbon, 1.51 mmol, 0.25 equiv) and ammonium formate (3.8 g, 60.3 mmol, 10.0 equiv). The mixture was heated to reflux for 2 hours. The solution was then cooled at room temperature and filtered through Celite. The filtrate was concentrated and the residue was purified by silica gel column chromatography, acetone/heptane 50% to give product 1.05 g (96% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography, acetone/heptane 50%

Sources & evidence

ORD record
ord-82dece2aa6494535b21f4b5f179cacc7
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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