Reaction #68786

Reaction equation

3-(4-cyclopropylmethoxy-phenoxy)-azetidine

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

NaOtBu

2-(di-tert-butylphosphino)biphenyl

→

desired product

(1-{4-[3-(4-Cyclopropylmethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethyl)-carbamic acid tert-butyl ester

Solvents

1,4-dioxane

Conditions

Workup

1. 1
   FiltrationThe mixture is filtered
2. 2
   Washwashed with MeOH
3. 3
   Concentrationconcentrated
4. 4
   OtherThe residue is purified by HPLC (silica gel; PE/ethyl acetate; gradient 9:1→1:1)

Procedure

To 0.9 g (4.1 mmol) 3-(4-cyclopropylmethoxy-phenoxy)-azetidine (IX.1), 1.2 g (4.1 mmol) (S)-[1-(4-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (I.3), 1.6 g (16.4 mmol) NaOtBu, 0.49 g (1.64 mmol) 2-(di-tert-butylphosphino)biphenyl and 0.38 g (0.41 mmol) tris-(dibenzylideneacetone)-dipalladium(0) are added under an argon atmosphere 25 mL 1,4-dioxane. The mixture is stirred for 12 h at 45° C. The mixture is filtered, washed with MeOH and concentrated. The residue is purified by HPLC (silica gel; PE/ethyl acetate; gradient 9:1→1:1) to yield the desired product.

Source