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 then 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 filtrate residue was taken up in ethyl acetate and washed twice with aqueous ammonium chloride solution. The organic phase was dried over magnesium sulphate 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. washwashed twice with aqueous ammonium chloride solution
5. dry with materialThe organic phase was dried over magnesium sulphate
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-7e52cb3843cd4d4787f4985b38369b21

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018258B2