Acetic Acid → HCID 66812215, compound

HRID 2366561Notes

Reaction equation

HRID 2366561 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][C@H:7]([NH:15][C@@H](C3C=CC=CC=3)C)[CH2:6][C:5]2=1.CO.CC(O)=O>C1COCC1.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][C@H:7]([NH2:15])[CH2:6][C:5]2=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 67427914HCID 67427914, compound

Product 1

HCID 66812215HCID 66812215, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a degassed solution of (S)-6-fluoro-N—((R)-1-phenylethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-amine (8.96 g, 0.029 mol) in a mixture of THF (60 ml), MeOH (20 ml) and AcOH (10 ml) was added 20% Pd(OH)2 (1.34 g). The mixture was evacuated three times and the reaction was set under 1 atm (balloon) H2. It was stirred at rt for 10 h and filtered over celite. The pad was rinsed with THF/MeOH and the filtrate was concentrated to 50 ml. The residue was dissolved in EA, and washed with 1N NaOH. The aqueous phase was extracted with EA and the combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound as a white solid.

Workup

  1. customThe mixture was evacuated three times
  2. filtrationfiltered over celite
  3. washThe pad was rinsed with THF/MeOH
  4. concentrationthe filtrate was concentrated to 50 ml
  5. dissolutionThe residue was dissolved in EA
  6. washwashed with 1N NaOH
  7. extractionThe aqueous phase was extracted with EA
  8. dry with materialthe combined organic phases were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d298656ff9004e05b2c1f8597601e605
Source dataset
uspto-grants-2014_04
Patent number
US08697869B2

Reaction notes

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