tert-Butyl 1-[3-(benzylamino)-4-chlorobenzyl]cyclopropanecarboxylate → tert-Butyl 1-(3-amino-4-chlorobenzyl)cyclopropanecarboxylate
Reaction equation
C([NH:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=1[Cl:26])[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(OCC)(=O)C.[Pd]>[NH2:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:12][C:13]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]1Participants
4
Procedure
50.0 g (134.4 mmol) of tert-butyl 1-[3-(benzylamino)-4-chlorobenzyl]cyclopropanecarboxylate were dissolved in 1.5 liters of ethyl acetate, and 1.43 g (1.34 mmol) of palladium (10% on carbon) were added. The reaction mixture was stirred at RT under a hydrogen atmosphere at standard pressure overnight. The reaction mixture was then filtered off with suction through kieselguhr, and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (mobile phase petroleum ether/ethyl acetate 10:1). The resulting product was stirred in a methanol/water mixture (70:30) and the solid was isolated. 24.3 g (64.1% of theory) of the target compound were obtained.
Workup
- filtrationThe reaction mixture was then filtered off with suction through kieselguhr
- concentrationthe filtrate was concentrated
- customThe crude product was purified by chromatography on silica gel (mobile phase petroleum ether/ethyl acetate 10:1)
- stirringThe resulting product was stirred in a methanol/water mixture (70:30)
- customthe solid was isolated
- custom24.3 g (64.1% of theory) of the target compound were obtained
Sources & evidence
- ORD record
- ord-490613a1bcb448629ee3d8bbccaa5500
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309198B2
Reaction notes
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