Perchloric Acid → Methyl 4-(2-amino-indan-5-yl)-butyrate

HRID 1651855Notes

Reaction equation

HRID 1651855 reaction equation
Cl(O)(=O)(=O)=O.[NH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:16](=O)[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:13]=2)[CH2:8]1.[H][H]>C(O)(=O)C.[Pd]>[NH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:13]=2)[CH2:8]1

Participants

6

Reactant 3

HCID 24247Perchloric AcidHCID 14071498Methyl 4-(2-amino-indan-5-yl)-4-oxobutyrateHCID 178418361HCID 178418361, compound

Product 1

HCID 23050620Methyl 4-(2-amino-indan-5-yl)-butyrate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

3 ml of perchloric acid and 3 g of 10% palladium-on-charcoal are added to 15 g (52.8 mmol) of methyl 4-(2-amino-indan-5-yl)-4-oxobutyrate in 200 ml of glacial acetic acid and the mixture is hydrogenated at 50° C. and a hydrogen pressure of 5 bar. When the calculated amount of hydrogen has been absorbed, the catalyst is filtered off, the filtrate is evaporated, sodium hydroxide is added to the residue and the reaction product is extracted with ether. After drying and evaporation, the desired product is obtained in the form of an oil.

Workup

  1. customis hydrogenated at 50° C.
  2. customWhen the calculated amount of hydrogen has been absorbed
  3. filtrationthe catalyst is filtered off
  4. customthe filtrate is evaporated
  5. additionsodium hydroxide is added to the residue
  6. extractionthe reaction product is extracted with ether
  7. customAfter drying
  8. customevaporation

Sources & evidence

ORD record
ord-6ff5c21a3bc04e53816695c7d81cbdcf
Source dataset
uspto-grants-1990_05
Patent number
US04929754

Reaction notes

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