(+/-)-tert-Butyl 1-{[3-(benzylamino)-4-chlorophenyl](methoxy)methyl}cyclopropanecarboxylate → (+/-)-tert-Butyl 1-[(3-amino-4-chlorophenyl)(methoxy)methyl]cyclopropanecarboxylate
Reaction equation
C([NH:8][C:9]1[CH:10]=[C:11]([CH:16]([O:27][CH3:28])[C:17]2([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18]2)[CH:12]=[CH:13][C:14]=1[Cl:15])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[NH2:8][C:9]1[CH:10]=[C:11]([CH:16]([O:27][CH3:28])[C:17]2([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:18][CH2:19]2)[CH:12]=[CH:13][C:14]=1[Cl:15]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
6.20 g (15.4 mmol) of (+/−)-tert-butyl 1-{[3-(benzylamino)-4-chlorophenyl](methoxy)methyl}-cyclopropanecarboxylate were dissolved in 300 ml of ethyl acetate and inertized with argon, and 350 mg of palladium (10% on carbon) were added. At RT, the reaction mixture was stirred for a total of 24 h under an atmosphere of hydrogen at atmospheric pressure. The reaction mixture was then filtered through Celite, the residue was washed thoroughly with ethyl acetate and the combined filtrate was concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 30:1→10:1). This gave 3.36 g of the target compound (69.9% of theory).
Workup
- additionwere added
- filtrationThe reaction mixture was then filtered through Celite
- washthe residue was washed thoroughly with ethyl acetate
- concentrationthe combined filtrate was concentrated under reduced pressure
- customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 30:1→10:1)
Sources & evidence
- ORD record
- ord-0446f913827744b7a20fd5d7a9bd60d9
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018258B2
Reaction notes
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