Cyclohexane ethylacetate → Methyl [1-(3-amino-4-fluorophenyl)cyclopropyl]acetate

HRID 1476058Notes

Reaction equation

HRID 1476058 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[CH:10]=[C:11]([C:16]2([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:18][CH2:17]2)[CH:12]=[CH:13][C:14]=1[F:15])C1C=CC=CC=1.C1CCCCC1.C(OCC)(=O)C>[Pd].C(O)C>[NH2:8][C:9]1[CH:10]=[C:11]([C:16]2([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:17][CH2:18]2)[CH:12]=[CH:13][C:14]=1[F:15]

Participants

5

Reactant 2

HCID 21867204Cyclohexane ethylacetateHCID 58288425Methyl {1-[3-(dibenzylamino)-4-fluorophenyl]cyclopropyl}acetate

Product 1

HCID 58288274Methyl [1-(3-amino-4-fluorophenyl)cyclopropyl]acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

At room temperature, 200 mg of palladium on carbon (10%) were added to a solution of 2.1 g (5.2 mmol) of methyl {1-[3-(dibenzylamino)-4-fluorophenyl]cyclopropyl}acetate in 100 ml of ethanol, and the mixture was hydrogenated at atmospheric pressure for 12 h. After the reaction had gone to completion (monitored by TLC; mobile phase cyclohexane/ethyl acetate 1:1), the reaction solution was filtered through kieselguhr and the filtrate was concentrated under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 647 mg (2.9 mmol, 56% of theory) of the title compound.

Workup

  1. filtrationthe reaction solution was filtered through kieselguhr
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-8637bce0a7cf463594351e7d9aec2699
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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