Ethyl 4-piperidinecarboxylate → HCID 69025828, compound

Participants

Reaction Conditions

Reaction Steps

In a round-bottom flask, 20 ml of anhydrous toluene is added and degassed several times from vacuum/N2. 2-methoxy-5-bromopyridine (752 mg, 4.0 mmol), ethyl isonipecotate (740 mg, 4.8 mmol), sodium t-butoxide (537 mg, 5.6 mmol), Pd2(DBA)3 (73 mg, 2 mol %) and of BINAP (100 mg, 0.16 mmol) are added and heated to 70° C. under N2 for 16 hrs. The reaction is cooled to r.t. and taken up in 100 ml of ethyl ether and washed with brine (2×50 ml). The ether is dried over MgSO4, filtered and reduced to an oil under vacuum. The compound is purified by flash chromatography on silica gel using 20% ethyl acetate/hexane as the eluent to provide 6′-methoxy-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-4-carboxylic acid ethyl ester. 1H NMR (300 MHz, CDCl3) δ 7.78 (d, 1H), 7.28 (dd, 1H), 6.66 (d, 1H), 4.15 (q, 2H), 3.87 (s, 3H), 3.42 (dt, 2H), 2.71 (dt, 2H), 2.39 (m, 1H), 2.03 (m, 2H), 1.90 (m, 2H), 1.26 (t, 3H); MS (EI) 264 (M)+.

Provenance & Evidence