Ethylene → HCID 53709387, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropanamine (prepared as described in WO 94/11337, Example 1) (8 g, 12.7 mmol), Pd(OAc)2 (28 mg, 0.12 mmol), tri-o-tolyl-phosphine (74 mg, 0.14 mmol) and tributylamine (5.9 mL, 24.5 mmol) in dimethylacetamide (50 mL) was heated to 60° C. under nitrogen atmosphere. Ethene (g) was then added to 8 bars pressure. After stirring overnight the reaction mixture was allowed to cool to room temperature. Nitrogen was flushed through the reaction vessel, and toluene and water were added. The aqueous layer was extracted with toluene and the combined organic layers were dried (MgSO4) and concentrated. The residue was treated with sodium hydroxide (1 M) and extracted with diethyl ether and toluene. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silica (gradient ethyl acetate-methanol 90:10 up to 0.06% NH3 in ethyl acetate-methanol 90:10) Yield 1 g (18%); 1H NMR (CDCl3) δ0.94 (d, 12H), 2.20 (br, 2H), 2.37 (br, 2H), 3.0 (br, 2H), 4.38 (t, 1H), 5.0 (s, 2H), 5.11 (d, 1H), 5.61 (d, 1H), 6.60-6.70 (m, 1H), 6.80 (d, 1H), 7.12-7.19 (m, 12H).

Provenance & Evidence