Hydrochloric Acid → (3R,4R)-3-methylpiperidin-4-yl pivalate

HRID 1928988Notes

Reaction equation

HRID 1928988 reaction equation
C([N:8]1[CH2:13][CH2:12][C@@H:11]([O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[C@H:10]([CH3:21])[CH2:9]1)C1C=CC=CC=1.Cl>CO.[Pd]>[CH3:21][C@H:10]1[C@H: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 131728602trans-2,2-Dimethyl-propionic acid 1-benzyl-3-methyl-piperidin-4-yl ester

Product 1

HCID 59600263(3R,4R)-3-methylpiperidin-4-yl pivalate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The trans-ester 18 (104 g, 359 mmol) is hydrogenated in methanol (1700 ml) with Pd/C in the presence of one equivalent of HCl (431 ml, 359 mmol, 1.25M in MeOH). The mixture is filtered and evaporated. The residue is redissolved in ether and extracted with 1N-NaOH and brine. Evaporation gives a colourless oil.

Workup

  1. filtrationThe mixture is filtered
  2. customevaporated
  3. dissolutionThe residue is redissolved in ether
  4. extractionextracted with 1N-NaOH and brine
  5. customEvaporation
  6. customgives a colourless oil

Sources & evidence

ORD record
ord-3be307865666433cb8f3d30bfa591a17
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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