Ammonium formate → trans-3-(5-fluoro-1H-indol-3-yl)-cyclopentylamine

HRID 1072452Notes

Reaction equation

HRID 1072452 reaction equation
C([NH:8][C@H:9]1[CH2:13][CH2:12][C@H:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([F:23])[CH:21]=3)[NH:16][CH:15]=2)[CH2:10]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[F:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C@H:11]1[CH2:12][CH2:13][C@H:9]([NH2:8])[CH2:10]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68830416trans-benzyl-3-(5-fluoro-1H-indol-3-yl)-cyclopentylamine

Product 1

HCID 68827696trans-3-(5-fluoro-1H-indol-3-yl)-cyclopentylamineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of trans-benzyl-3-(5-fluoro-1H-indol-3-yl)-cyclopentylamine (0.45 g, 1.46 mmol), 0.20 g 10% Pd/C, and ammonium formate (1.0 g, 15.9 mmol) in methanol (30 mL) were refluxed under nitrogen for 4 hours. The reaction mixture was cooled, filtered through celite, and concentrated. The residue was diluted with 1 N aqueous NaOH (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), then were dried over anhydrous sodium sulfate, filtered, and concentrated to give 0.28 g (100%) of the title compound as a thick oil: MS (ESI) m/z 219 [M+H]+.

Workup

  1. temperaturewere refluxed under nitrogen for 4 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. additionThe residue was diluted with 1 N aqueous NaOH (50 mL)
  6. extractionextracted with ethyl acetate (3×50 mL)
  7. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
  8. dry with materialwere dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-acfa7053bfbf469abdfc8e3ad3dabba3
Source dataset
uspto-grants-2005_06
Patent number
US06911445B2

Reaction notes

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