Di-tert-butyl dicarbonate → Tert-butyl{2-[2'-(3-methoxypropyl)-3-methylbiphenyl-4-yl]-3-pyridin-3-ylpropyl}carbamate

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Reaction Steps

To a solution of 2-[2′-(3-methoxypropyl)-3-methylbiphenyl-4-yl]-3-pyridin-3-ylpropanenitrile from step 2 (1 eq.) in EtOH/THF (3:1; 0.1M) at room temperature was added cobaltous chloride hexahydrate (CoCl2.6H2O; 2 eq.), followed by (BOC)2O (2 eq.) and finally sodium borohydride (10 eq.) portionwise. The final black mixture was stirred for 3 h at room temperature, quenched with HCl (1N). The pH was adjusted to 8 using saturated aqueous Na2CO3 and the resulting mixture was extracted several times with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (10 to 75% in 30 min) afforded the desired compound as a colorless oil.

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