L-Tartaric acid → 2-Methyl-2-(2-methyl-5-piperidin-3-yl-phenoxy)-propionic acid ethyl ester l-tartaric acid salt

HRID 1269532Notes

Reaction equation

HRID 1269532 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([O:24][C:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])([CH3:27])[CH3:26])[CH:18]=2)[CH2:12]1)=O)C1C=CC=CC=1.[C:33]([OH:42])(=[O:41])[C@@H:34]([C@H:36]([C:38]([OH:40])=[O:39])[OH:37])[OH:35]>[Pd].C(O)C>[C:33]([OH:42])(=[O:41])[C@@H:34]([C@H:36]([C:38]([OH:40])=[O:39])[OH:37])[OH:35].[CH2:31]([O:30][C:28](=[O:29])[C:25]([CH3:27])([O:24][C:19]1[CH:18]=[C:17]([CH:13]2[CH2:14][CH2:15][CH2:16][NH:11][CH2:12]2)[CH:22]=[CH:21][C:20]=1[CH3:23])[CH3:26])[CH3:32]

Participants

5

Reactant 2

HCID 444305L-Tartaric acidHCID 688825133-[3-(1-Ethoxycarbonyl-1-methyl-ethoxy)-4-methyl-phenyl]-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 688846382-Methyl-2-(2-methyl-5-piperidin-3-yl-phenoxy)-propionic acid ethyl ester l-tartaric acid saltYield 57.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent3×

Procedure

A 250 mL Parr bottle was charged with 0.27 g of 10% palladium on carbon (50% water) and covered with 20 mL ethanol. 3-[3-(1-ethoxycarbonyl-1-methyl-ethoxy)-4-methyl-phenyl]-piperidine-1-carboxylic acid benzyl ester (1.36 g, 3.09 mmol) was dissolved in 50 mL ethanol and added to the catalyst suspension. The reaction was hydrogenated at 50 psi for 2 h. The catalyst was filtered through a celite plug. The filter cake was washed with 150 mL ethanol and the filtrated concentrated under reduced pressure. The resultant oil was taken up in 20 mL hot ethanol to which was added L-tartaric acid (464 mg, 3.09 mmol) in 10 mL hot ethanol. The solution was allowed to stir 24 h at ambient temperature. The white crystalline precipitate was collected by filtration to yield 805 mg (57%) of 2-methyl-2-(2-methyl-5-piperidin-3-yl-phenoxy)-propionic acid ethyl ester L-tartaric acid salt as a white crystalline solid.

Workup

  1. additionadded to the catalyst suspension
  2. filtrationThe catalyst was filtered through a celite plug
  3. washThe filter cake was washed with 150 mL ethanol
  4. concentrationthe filtrated concentrated under reduced pressure
  5. filtrationThe white crystalline precipitate was collected by filtration

Sources & evidence

ORD record
ord-831c19dec23f4b0c94eae7e22c64514b
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

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