rac-Ethyl 2-[3-(benzylamino)-4-fluorophenyl]-trans-cyclopropanecarboxylate → rac-Ethyl 2-[3-amino-4-fluorophenyl]-trans-cyclopropanecarboxylate

HRID 1476068Notes

Reaction equation

HRID 1476068 reaction equation
C([NH:8][C:9]1[CH:10]=[C:11]([C@@H:16]2[CH2:18][C@H:17]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:12]=[CH:13][C:14]=1[F:15])C1C=CC=CC=1.[H][H]>C(O)C.C1COCC1.[Pd]>[NH2:8][C:9]1[CH:10]=[C:11]([C@@H:16]2[CH2:18][C@H:17]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:12]=[CH:13][C:14]=1[F:15]

Participants

5

Reactant 2

HCID 123461582rac-Ethyl 2-[3-(benzylamino)-4-fluorophenyl]-trans-cyclopropanecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 123637899rac-Ethyl 2-[3-amino-4-fluorophenyl]-trans-cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

262 mg (purity 66%, 0.55 mmol) of (+/−)-ethyl 2-[3-(benzylamino)-4-fluorophenyl]-trans-cyclopropanecarboxylate were dissolved in 5 ml of ethanol/THF (1:1), 26 mg of palladium on carbon (10%) were added and the mixture was hydrogenated at RT using a hydrogen pressure of 1 bar for 24 h. The reaction mixture was then filtered through celite, the residue was washed with ethanol and the filtrate was concentrated. The crude product obtained in this manner was purified by preparative HPLC. This gave 87 mg (69% of theory) of the target compound.

Workup

  1. customwas hydrogenated at RT
  2. customfor 24 h
  3. filtrationThe reaction mixture was then filtered through celite
  4. washthe residue was washed with ethanol
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0395c158f5d54612a9a55dfaa91fc24b
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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