Water → (R)-7-hydroxy-3-(2-phthalimidopropyl)indole

HRID 1241230Notes

Reaction equation

HRID 1241230 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][C@H:19]([N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31])[CH3:20])C1C=CC=CC=1.O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][C@H:19]([N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31])[CH3:20]

Participants

6

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 58713922(R)-7-benzyloxy-3-(2-phthalimidopropyl)indole

Product 1

HCID 58713928(R)-7-hydroxy-3-(2-phthalimidopropyl)indole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

(R)-7-Benzyloxy-3-(2-phthalimidopropyl)indole 12.16 g was dissolved in 400 ml of ethanol, and a water 100 ml suspension of a 10% palladium on carbon catalyst (content 50%) 4.00 g prepared separately was added thereto. Ammonium formate 6.00 g was added thereto while stirring, and the suspension was heated in an oil bath of 95° C. For one hour. After cooling down, the catalyst was filtered off, and the filtrate was concentrated under reduced pressure. Acetone was added to the residue, and a deposited salt was filtered off. The filtrate was concentrated under reduced pressure, whereby 10.27 g of a residue containing the title compound was obtained.

Workup

  1. customprepared separately
  2. additionwas added
  3. temperatureAfter cooling down
  4. filtrationthe catalyst was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionAcetone was added to the residue
  7. filtrationa deposited salt was filtered off
  8. concentrationThe filtrate was concentrated under reduced pressure, whereby 10.27 g of a residue
  9. additioncontaining the title compound
  10. customwas obtained

Sources & evidence

ORD record
ord-9378539df71a45bc9c69d7fb62c595b5
Source dataset
uspto-grants-2006_10
Patent number
US07115412B2

Reaction notes

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