Benzaldehyde → (+/-)-{(2R*,4S*)-1-[(1R*)-4-Methyl-1-phenylpent-4-en-2-yn-1-yl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetic acid

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(±)-Methyl{(2R*,4S*)-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate (Example 3 Step 3, 150 mg, 0.5 mmol), benzaldehyde (159 mg, 1.5 mmol), gold (III) bromide (22 mg, 0.05 mmol) and water (0.5 ml) were combined in a sealed microwave tube. The mixture was de-gassed and placed under an N2-atmosphere before 2-methyl-1-buten-3-yne (99 mg, 1.5 mmol) was added via syringe, followed by heating to 70° C. using microwave irradiation for 20 min. The reaction mixture was diluted with MeOH and loaded onto a SCX cartridge, which was washed with MeOH, then eluted with 2M ammonia in MeOH. The eluant was treated with 6M aq. NaOH (0.25 ml) and heated to reflux for 2 h. The volatiles were removed under vacuum and the residue partitioned between 2M HCl and DCM. The DCM layer was evaporated and the residue purified by preparative reverse phase HPLC to give 21 mg of the title compound as the TFA salt.

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