Sodium borohydride → 2-(2'-Chloro-3-methyl-biphenyl-4-yl)-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-propylamine

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Reaction Steps

To a solution of 2-(2′-chloro-3-methylbiphenyl-4-yl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propanenitrile from step 4 (1 eq.) in MeOH/THF (4:1; 0.08M) at room temperature was added cobaltous chloride hexahydrate (CoCl2.6H2O; 2 eq.) and then portionwise sodium borohydride (10 eq.). The final black mixture was stiffed for 12 h at room temperature, poured in aqueous NaOH (1N) and diluted with EtOAc. The precipitate was filtered-off on celite and the organic extract was washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated. Purification by column chromatography on silica gel, eluting with CH2Cl2/MeOH(NH3 2M) 4%, afforded the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.52-7.48 (m, 1H); 7.40-7.25 (m, 6H); 7.11 (s, 2H); 6.98 (d, 2 H); 6.80 (d, 2H); 4.39-4.32 (m, 4H); 3.35 (m, 1H); 3.10 (m, 2H); 3.0-2.75 (m, 4H); 2.30 (s, 3 H); 2.20 (s, 3H).

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