Reacción #68785

Ecuación de reacción

3-(4-ethoxy-phenoxy)-azetidine

(S)-[1-(4-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester

KOtBu

2-(di-tert-butylphosphino)biphenyl

→

desired product

(S)-1-{4-[3-(4-Ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamine

Disolventes

1,4-dioxane

water

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónthe mixture is filtered
2. 2
   Concentraciónconcentrated in vacuo
3. 3
   Lavadois washed with water
4. 4
   ConcentraciónThe organic layer is concentrated
5. 5
   Otrothe residue is purified by HPLC (eluent A: water+0.1% NH4OH, eluent B: MeOH)

Procedimiento

To 5.0 g (21.8 mmol) 3-(4-ethoxy-phenoxy)-azetidine and 6.5 g (21.8 mmol) (S)-[1-(4-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (1.3) in 80 mL 1,4-dioxane under an argon atmosphere are added 8.6 g (87.1 mmol) KOtBu, 0.65 g (2.18 mmol) 2-(di-tert-butylphosphino)biphenyl and 1.0 g (1.09 mmol) tris-(dibenzylideneacetone)-dipalladium(0). The mixture is stirred for 2 h at 120° C. Subsequently 200 mL MeOH and 5 mL water are added and the mixture is filtered and concentrated in vacuo. The residue is taken up in ethyl acetate and is washed with water. The organic layer is concentrated and the residue is purified by HPLC (eluent A: water+0.1% NH4OH, eluent B: MeOH) to yield the desired product.

Fuente