pentan-3-ylbenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of amine (from Example 104, Step E) and (±) -1, 5-dibromo, 3-phenyl-pentane in 0.5 mL of isobutylnitrile was added 0.080 mL of DIEA and a catalytic amount of tetrabutyl-ammonium iodide. After warming the reaction to 95° C. for 22 h, the mixture was partitioned between 10 mL of CH2Cl2 and 10 mL 1N NaOH. After separating layers, the aqueous phase was extracted with 10 mL of CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated under vacuum. The residue was purified by flash chromatography eluting with 10% EtOAc in hexanes to provide 10 mg of the title compound: 1H NMR (300 MHz, CDCl3): δ1.2-1.9 (m, 16H), 2.1-2.4 (m, 2H), 2.6-3.0 (m, 6H), 4.0-4.4 (m, 2H), 7.0-7.4 (m, 10H). RF : 0.45 (20% EtOAc in hexanes). After warming the reaction to 95° C. for 22 h the mixture was partitioned between 10 mL of CH2Cl2 and 10 mL 1N NaOH After separating layers the aqueous phase was extracted with 10 mL of CH2Cl2 The combined organic layers were dried over Na2SO4 concentrated under vacuum The residue was purified by flash chromatography eluting with 10% EtOAc in hexanes