3,6-dihydro-2H-[4,4]bipyridinyl-1,3'-dicarboxylic acid 1-t-butyl ester 3'-methyl ester → Methyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)nicotinate

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Reaction Steps

A solution of Pd(OH)2/C (5.2 g, 7.4 mmol, 0.3 eq., 20%) in EtOAc (100 mL) was stirred for 10 minutes at room temperature under nitrogen. 3,6-Dihydro-2H-[4,4′]bipyridinyl-1,3′-dicarboxylic acid 1-t-butyl ester 3′-methyl ester (8.7 g, 27.3 mmol, 1.0 eq.) was added. Hydrogen gas was introduced into the reaction vessel (at 1 atm) and the solution was stirred for 5 hours at room temperature. The solids were filtered and the resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with EtOAc/PE (1:5) to yield 3,4,5,6-tetrahydro-2H-[4,4′]bipyridinyl-1,3′-dicarboxylic acid 1-t-butyl ester 3′-methyl ester (6.7 g) as a colorless oil.

Provenance & Evidence