Triphenylphosphine → Tert-butyl 4-[6-(4-cyclohexyl-3-trifluoromethyl-phenoxymethyl)-pyridin-3-yl]-piperazine-1-carboxylate

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Reaction Steps

tert-Butyl 4-(6-hydroxymethyl-pyridin-3-yl)-piperazine-1-carboxylate (0.22 mmol), 4-Cyclohexyl-3-trifluoromethyl-phenol (0.22 mmol, synthesized in a similar manner as described in a previous example), 1,1′-azodicarbonyl dipiperdine (0.33 mmol) and Ph3P (0.33 mmol) are mixed in DCM (2 mL). The reaction mixture is stirred at room temperature for 17 h and then partitioned between saturated Na2CO3 solution and EtOAc. The aqueous phase is extracted with EtOAc. The combined organic extracts are washed with saturated aqueous NaCl and dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (6:5 hexanes/EtOAc) to give tert-butyl 4-[6-(4-cyclohexyl-3-trifluoromethyl-phenoxymethyl)-pyridin-3-yl]-piperazine-1-carboxylate.

Provenance & Evidence