tert-Butyl 1-[3-(benzylamino)benzyl]cyclopropanecarboxylate → tert-Butyl 1-(3-aminobenzyl)cyclopropanecarboxylate

HRID 877206Notes

Reaction equation

HRID 877206 reaction equation
C([NH:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[CH2:12][C:13]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]1)C1C=CC=CC=1>C(O)C.C1COCC1.[Pd]>[NH2:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[CH2:12][C:13]1([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:15][CH2:14]1

Participants

5

Reactant 1

HCID 58136299tert-Butyl 1-[3-(benzylamino)benzyl]cyclopropanecarboxylate

Product 1

HCID 58136514tert-Butyl 1-(3-aminobenzyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

6.98 g (22.43 mmol) of tert-butyl 1-[3-(benzylamino)benzyl]cyclopropanecarboxylate were dissolved in 50 ml of ethanol and 50 ml of THF, and 0.48 g (0.45 mmol) of palladium (10% on carbon) were added. At RT, the mixture was stirred under an atmosphere of hydrogen at atmospheric pressure for 2 h. The reaction mixture was then filtered off with suction through kieselguhr, the residue was washed with THF and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 3.66 g (65.9% of theory) of the title compound.

Workup

  1. filtrationThe reaction mixture was then filtered off with suction through kieselguhr
  2. washthe residue was washed with THF
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-13a73e931b824dd0aa2ac7f5a6310de9
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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