Acetic Acid → HCID 86710548, compound

HRID 1027154Notes

Reaction equation

HRID 1027154 reaction equation
[OH:1][C@H:2]([C@H:4]1[N:9](CC2C=CC(OC)=CC=2)[C:8]([CH3:20])([CH3:19])[CH2:7][C:6](=[O:21])[CH2:5]1)[CH3:3].C(O)(=O)C>CO.[OH-].[Pd+2].[OH-]>[OH:1][C@H:2]([C@H:4]1[NH:9][C:8]([CH3:20])([CH3:19])[CH2:7][C:6](=[O:21])[CH2:5]1)[CH3:3]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86710545HCID 86710545, compound

Product 1

HCID 86710548HCID 86710548, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-6-((S)-1-hydroxyethyl)-1-(4-methoxybenzyl)-2,2-dimethylpiperidin-4-one (0.28 g, 0.96 mmol) in MeOH (40 mL) was added acetic acid (0.055 mL, 0.96 mmol) and palladium hydroxide (0.13 g, 0.96 mmol). After degassing, the mixture was stirred overnight under hydrogen. The mixture was filtered through the celite, washed with MeOH (20 mL), and concentrated in vacuo to give 0.11 g (67%) of (S)-6-((S)-1-hydroxyethyl)-2,2-dimethylpiperidin-4-one which was used in the next step without purification.

Workup

  1. customAfter degassing
  2. filtrationThe mixture was filtered through the celite
  3. washwashed with MeOH (20 mL)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b7ee08a08e9f4895b08f13796ac496d6
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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