HCID 6324716, compound → HCID 57889377, compound

HRID 1820232Notes

Reaction equation

HRID 1820232 reaction equation
[OH:1][C@H:2]1[C@H:6]([CH3:7])[CH2:5][C@@H:4]([C:8]([O:10]CC2C=CC=CC=2)=[O:9])[CH2:3]1.O[C@@H]1[C@@H](C)C[C@H](C(OCC2C=CC=CC=2)=O)C1.O[C@H]1[C@H](C)C[C@@H](C(O)=O)C1>CO.[OH-].[OH-].[Pd+2]>[OH:1][C@@H:2]1[C@@H:6]([CH3:7])[CH2:5][C@H:4]([C:8]([OH:10])=[O:9])[CH2:3]1

Participants

6

Reactant 3

HCID 6324716HCID 6324716, compoundHCID 57888735HCID 57888735, compoundHCID 57889867HCID 57889867, compound

Product 1

HCID 57889377HCID 57889377, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A racemic mixture of (1R,3R,4R)-benzyl 3-hydroxy-4-methylcyclopentanecarboxylate and (1S,3S,4S)-benzyl 3-hydroxy-4-methylcyclopentanecarboxylate (217 mg, 0.463 mmol) and palladium hydroxide on carbon (65.0 mg, 0.463 mmol) in methanol (10 mL) was degassed under vacuum/nitrogen, and the mixture was hydrogenated overnight at 50 psi. The catalyst was removed by filtration and rinsed with methanol. The filtrates were combined and concentrated in-vacuo to yield a racemic mixture of (1R,3R,4R)-3-hydroxy-4-methylcyclopentanecarboxylic acid and (1S,3S,4S)-3-hydroxy-4-methylcyclopentanecarboxylic acid (131 mg, 0.454 mmol, 98% yield) as a colorless oil which solidified upon standing overnight.

Workup

  1. customwas degassed under vacuum/nitrogen
  2. customThe catalyst was removed by filtration
  3. washrinsed with methanol
  4. concentrationconcentrated in-vacuo
  5. customto yield

Sources & evidence

ORD record
ord-f5ec06c4ab7449b2ad562cbffff5ded1
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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