Hydrochloric Acid → 2,2-Dimethyl-propionic acid (3RS,4RS)-3-methyl-piperidin-4-yl ester

HRID 1804760Notes

Reaction equation

HRID 1804760 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH:10]([CH3:21])[CH2:9]1)C1C=CC=CC=1.Cl>CO.[OH-].[Pd+2].[OH-]>[CH3:21][CH:10]1[CH:11]([O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 668417832,2-Dimethyl-propionic acid (3RS,4RS)-1-benzyl-3-methyl-piperidin-4-yl ester

Product 1

HCID 668421342,2-Dimethyl-propionic acid (3RS,4RS)-3-methyl-piperidin-4-yl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

Palladium hydroxide (20% on carbon, 1.5 g) is placed in a round-bottom flask under an argon atmosphere and covered with methanol, A solution of 2,2-dimethyl-propionic acid (3RS,4RS)-1-benzyl-3-methyl-piperidin-4-yl ester (4) (15 g, 51.8 mmol) in 300 ml of methanol is added, followed by an 1.3M methanolic HCl solution (62 ml, 78 mmol). Then the mixture is hydrogenated under normal pressure for 20 h. The solution is filtrated through celite and evaporated under reduced pressure. The residue is dissolved in diethyl ether and washed with 1N aqueous sodium hydroxide solution and brine. The combined organic layers are dried over Na2SO4 and evaporated under reduced pressure.

Workup

  1. filtrationThe solution is filtrated through celite
  2. customevaporated under reduced pressure
  3. dissolutionThe residue is dissolved in diethyl ether
  4. washwashed with 1N aqueous sodium hydroxide solution and brine
  5. dry with materialThe combined organic layers are dried over Na2SO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-dfe6ecf1565c49deb091fc4df364aa91
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

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