HCID 20256923, compound → HCID 20256917, compound

HRID 637382Notes

Reaction equation

HRID 637382 reaction equation
[CH2:1]([CH:3]([C:9](O)([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:10][CH3:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]>C(O)(=O)C.CS(O)(=O)=O.[Pd]>[CH2:1]([CH:3]([CH:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:10][CH3:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 20256923HCID 20256923, compound

Product 1

HCID 20256917HCID 20256917, compound

Reagents, catalysts & solvents 3

HCID 6395Methanesulfonic AcidCatalystHCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

10.7 g (0.038 mol) of ethyl 2-ethyl-3-hydroxy-3-(p-methoxyphenyl)pentanoate were hydrogenated in acetic acid (88 ml) solution in the presence of methanesulfonic acid (7 drops) by using 10% Pd-C as catalyst. The catalyst was filtered off and the solvent was evaporated. The product was dissolved in methylene chloride, washed with diluted potassium carbonate and water and dried. After evaporation of the solvent 9,5 g (97%) of the product as a mixture of erythro and threo diastereomers were obtained.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated
  3. dissolutionThe product was dissolved in methylene chloride
  4. washwashed with diluted potassium carbonate and water
  5. customdried
  6. customAfter evaporation of the solvent 9,5 g (97%) of the product
  7. additionas a mixture of erythro
  8. customthreo diastereomers were obtained

Sources & evidence

ORD record
ord-971d6de2d4a7496897d5fd9b628b99f8
Source dataset
uspto-grants-1985_12
Patent number
US04556677

Reaction notes

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