Acetic Acid → [4-(2-Methoxy-5-pyridin-4-yl-benzylamino)-cyclohexyl]-carbamic acid tert-butyl ester

Participants

Reaction Steps

A stirred suspension of amine (295) (131 mg, 0.61 mmol) and aldehyde (296) (130 mg, 0.61 mmol) in THF (1 mL) and toluene (1 mL) was treated with AcOH (42 μL, 0.73 mmol) at RT. After stirring 1.5 h, the resultant suspension was treated with sodium triacetoxyborohydride (181 mg, 0.86 mmol) and stirred for 18 h. The reaction was diluted with aqueous NaHCO3 and extracted into EtOAc. The organic phase was dried (Na2SO4), filtered, the solvent removed in vacuo and the residue chromatographed with 10% MeOH in EtOAc to afford the title compound.

Provenance & Evidence