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

HRID 2267688Notes

Reaction equation

HRID 2267688 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-7a4687c3c03e4e63924ddf9a5848a518
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

Loading…