4,4'-Bis(1,1-dimethylethyl)-1,1'-biphenyl → 2-(3-Fluorophenyl)pyrrolidine

In step 9-2, 3-chloro-N-(3-fluorobenzylidene)propan-1-amine (9-1) (53 g, 266 mmol) was added at −78° C. to a solution of lithium granules (5.5 g, 800 mmol) and 4,4′-di-tert-butylbiphenyl (5.7 g, 21 mmol) in THF (50 mL) cooled to −78° C. The resulting solution was stirred at −78° C. for 2 hours then quenched with water and the temperature was allowed to rise up to 20° C. The solids were removed by filtration and the mother liquor was reduced using a rotary evaporator. The resulting residue was reconstituted in ethyl acetate, the organic washed with 1N HCl (3×25 mL) and the aqueous layer was extracted with ethyl acetate. The aqueous layer was then neutralized with 1N NaOH solution and the aqueous layer was extracted with ethyl acetate (3×100 mL). The organic layer was dried with sodium sulfate and the solvent was removed to yield 2-(3-fluorophenyl)pyrrolidine (9-2) as a light yellow oil. m/z=165.2 [M+1].