1-Phenylmethyl-alpha,alpha-dimethyl-1,2,3,6-tetrahydro-4-pyridine-acetic acid ethyl ester → Ethyl 2-methyl-2-(piperidin-4-YL)propanoate

HRID 557694Notes

Reaction equation

HRID 557694 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]([C:8]1[CH2:9][CH2:10][N:11](CC2C=CC=CC=2)[CH2:12][CH:13]=1)([CH3:7])[CH3:6])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:21])[C:5]([CH3:7])([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[CH3:6])[CH3:2]

Participants

4

Reactant 1

HCID 545483681-Phenylmethyl-alpha,alpha-dimethyl-1,2,3,6-tetrahydro-4-pyridine-acetic acid ethyl ester

Product 1

HCID 49759624Ethyl 2-methyl-2-(piperidin-4-YL)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-methyl-propionic acid ethyl ester from above (1.15 g, 4.0 mmol) was dissolved in 50 mL of ethanol and 10% palladium on carbon (600 mg) was added. The mixture was hydrogenated at 50 psi for 20 hrs. The mixture was filtered and solvents were evaporated to give 2-methyl-2-piperidin-4-yl-propionic acid ethyl ester (760 mg) as an oil. The NMR spectrum obtained on the sample is compatible with its structure. LRMS calcd for C11H21NO2 (m/e) 199.29, obsd 200.1 (M+H).

Workup

  1. filtrationThe mixture was filtered
  2. customsolvents were evaporated

Sources & evidence

ORD record
ord-91e1736e92764c77816a5b6151a1ed57
Source dataset
uspto-grants-2011_11
Patent number
US08058299B2

Reaction notes

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