Reaktion #68777

Reaktionsgleichung

(S)—N-[1-(4-bromo-phenyl)-ethyl]-acetamide

3-(tert-butyl-dimethyl-silanyloxy)-azetidine

NaOtBu

2-(di-tert-butylphosphino)biphenyl

→

desired product

(S)—N-(1-{4-[3-(tert-Butyl-dimethyl-silanyloxy)-azetidin-1-yl]-phenyl}-ethyl)-acetamide

Lösungsmittel

MeOH

water

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONare added
2. 2
   Filtrationthe mixture is filtered
3. 3
   Einengenconcentrated in vacuo
4. 4
   Sonstigedirectly purified by HPLC (column: XbridgeC18; eluent A: water+0.3% NH4OH, eluent B: MeOH)

Vorschrift

A mixture of 3.0 g (12.4 mmol) (S)—N-[1-(4-bromo-phenyl)-ethyl]-acetamide (I.1), 2.3 g (12.4 mmol) 3-(tert-butyl-dimethyl-silanyloxy)-azetidine (US2008/214520A1), 4.9 g (97%, 49.6 mmol) NaOtBu, 1.48 g (4.96 mmol) 2-(di-tert-butylphosphino)biphenyl and 1.1 g (1.24 mmol) tris-(dibenzylideneacetone)-dipalladium(0) in 30 mL 1,4-dioxane is stirred for 45 min under microwave irradiation at 80° C. After cooling water and MeOH are added, the mixture is filtered, concentrated in vacuo and directly purified by HPLC (column: XbridgeC18; eluent A: water+0.3% NH4OH, eluent B: MeOH) to yield the desired product.

Quelle