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

Temperature

110 °C

Under argon and dry conditions, 13.3 g (42.73 mmol) of tert-butyl 1-(3-bromobenzyl)-cyclopropanecarboxylate, 5.6 ml (51.28 mmol) of benzylamine, 1.96 g (2.14 mmol) of tris-(dibenzylideneacetone)dipalladium, 4.93 g (51.28 mmol) of sodium tert-butoxide and 1.06 g (1.71 mmol) of (+/−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl were suspended in 50 ml of toluene. The reaction mixture was stirred at 110° C. for 1.5 h. The mixture was then filtered off with suction through kieselguhr, the residue was washed with toluene and the filtrate was concentrated. The residue of the filtrate was taken up in ethyl acetate and extracted twice with ammonium chloride solution. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 20:1). This gave 6.98 g (48.4% of theory) of the title compound.

1. filtrationThe mixture was then filtered off with suction through kieselguhr
2. washthe residue was washed with toluene
3. concentrationthe filtrate was concentrated
4. extractionextracted twice with ammonium chloride solution
5. dry with materialThe organic phase was dried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 20:1)

ORD record

ord-1564f766b00c412fba54b57196ac2f6a

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987256B2