HCID 54092582, compound → HCID 15546658, compound

HRID 1978131Notes

Reaction equation

HRID 1978131 reaction equation
[CH3:1][O:2][CH2:3][O:4][C@H:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1)[C:6]([O:8]CC1C=CC=CC=1)=[O:7].[H][H]>CO.[C].[Pd]>[CH3:1][O:2][CH2:3][O:4][C@H:5]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)=[CH:21][CH:22]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 54092582HCID 54092582, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15546658HCID 15546658, compoundYield 113.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl (R)-2-methoxymethoxy-3-(4-morpholinophenyl)propionate (1.66 g) in methanol (8.6 ml) was added 10% palladium-carbon (0.2 g), and hydrogenation was carried out in a hydrogen atmosphere at atmospheric pressure and room temperature for 100 minutes. After the catalyst was filtered off, the solvent was distilled off under reduced pressure. The residue was further subjected to azeotropic distillation with isopropyl ether-hexane to provide 1.44 g of (R)-2-methoxymethoxy-3-(4-morpholino-phenyl)propionic acid.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. distillationThe residue was further subjected to azeotropic distillation with isopropyl ether-hexane

Sources & evidence

ORD record
ord-81540627945d487095e7c1716298eafc
Source dataset
uspto-grants-2001_05
Patent number
US06235875B1

Reaction notes

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