HCID 11021963, compound → HCID 15923158, compound

HRID 1978082Notes

Reaction equation

HRID 1978082 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([OH:15])=[O:14])[CH2:9][CH:10]=[CH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([C@H:8]([C@@H:12]([CH2:16][CH:17]([CH3:18])[CH3:19])[C:13]([OH:15])=[O:14])[CH2:9][CH2:10][CH3:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 11021963HCID 11021963, compound

Product 1

HCID 15923158HCID 15923158, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3.0 g of 2(R)-[1(S)-(tertbutoxycarbonyl)-3-butenyl]-4-methylvaleric acid in 30 ml of ethanol was hydrogenated in the presence of 0.3 g of 5% palladium-on-carbon for 4 hours. The catalyst was removed by filtration and the solvent was evaporated. The residue was dissolved in 30 ml of toluene and the solvent was evaporated again. Repetition of this procedure gave 2.83 g of 2(R)-[1(S)-(tertbutoxycarbonyl)-butyl]-4-methyl-valeric acid as a colourless oil.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in 30 ml of toluene
  4. customthe solvent was evaporated again

Sources & evidence

ORD record
ord-8cef77458ae04343bd21506161c0b53b
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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