Reaktion #68785

Reaktionsgleichung

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

Lösungsmittel

1,4-dioxane

water

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe mixture is filtered
2. 2
   Einengenconcentrated in vacuo
3. 3
   Waschenis washed with water
4. 4
   EinengenThe organic layer is concentrated
5. 5
   Sonstigethe residue is purified by HPLC (eluent A: water+0.1% NH4OH, eluent B: MeOH)

Vorschrift

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.

Quelle