Methyl iodide → N-(6-formyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-3-[methyl-(3-trifluoromethyl-benzenesulfonyl)-amino]-3-phenyl-propionamide

Participants

Reaction Steps

The aldehyde, N-(6-formyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-3-phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide (0.11 g), was stirred in dry DMF (5 mL) with sodium carbonate (0.2 g) and methyl iodide (0.2 mL) at RT for 3 days. Aqueous workup gave the crude product, N-(6-formyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-3-[methyl-(3-trifluoromethyl-benzenesulfonyl)-amino]-3-phenyl-propionamide (0.12 g). MS: 545.1 (M+1). This aldehyde (0.12 g) was converted to 3-[methyl-(3-trifluoromethyl-benzenesulfonyl)-amino]-3-phenyl-N-(6-piperidin-1-ylmethyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-propionamide using the general reductive amination conditions (amine, NaBH(OAc)3, RT, DCE) described earlier in this application. MS: 614.1 (M+1).

Provenance & Evidence