1-bromo-4-(3-methoxypropyl)benzene

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,4-Dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one (276 mg, obtained in example 121, step 3) was dissolved in DMF (18 mL) at r.t. Then, 1-bromo-4-(3-methoxy-propyl)-benzene (599 mg, obtained in example 130, step 2), N,N′-dimethylethylenediamine (sym) (230 mg), Cuprous iodide (373 mg) and K3PO4 (832 mg) were added to the reaction mixture and the mixture was heated to 80° C. for 3 hours. The reaction mixture was cooled, poured into ice/water and was extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The title compound was obtained as a yellow liquid (460 mg, 93%) and was used without further purification. MS (m/e): 360.2. [MH+]. The reaction mixture was cooled was extracted two times with ethyl acetate The combined organic layers were washed with brine dried over Na2SO4 filtered the solvent was evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-(4-Bromo-phenyl)-propan-1-ol (2.60 g, obtained in example 130, step 1) was dissolved in THF (35 mL). The mixture was cooled to 0° C. and sodium hydride (60% in mineral oil, 967 mg) was added in four portions to the cold mixture. Stirring was continued at 0° C. for 1 hour. Then, iodomethane (1.13 mL) was added dropwise over a period of 15 minutes to the reaction mixture. The mixture was warmed to room temperature over a period of 1 hour. The reaction mixture was poured into ice/water and was extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a light yellow liquid (2.61 g, 94%). MS (EI): 229.0 [M−]. The mixture was warmed to room temperature over a period of 1 hour was extracted two times with ethyl acetate The combined organic layers were washed with brine dried over Na2SO4 filtered the solvent was evaporated The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)