Acetic Acid → HCID 66649755, compound

Participants

Reaction Steps

To 1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinone (Example 57, step B) (0.63 g, 2.5 mmol), 1,1-dimethylethyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1.0 g, 5.0 mmol), HOAc (0.23 g, 3.8 mmol), TEA (0.25 g, 2.5 mmol) in DCM (20 mL) is added sodium triacetoxyborohydride (0.81 g, 3.8 mmol). The mixture was stirred for 1 h then poured into saturated NaHCO3 solution (30 mL). The layers are separated and the aqueous layer washed with DCM. The organics are combined, dried (MgSO4), filtered and rotovaped. DCM and silica are added and the solvent removed by rotovap. After purification by silica gel chromatography, the title compound of step A (1.0 g, 2.4 mmol, 96%) is obtained as a yellow foam. 1H NMR (400 MHz, CDCl3) δ 7.97 (d, J=9.3 Hz, 1H), 6.39 (dd, J=9.3, 2.0 Hz, 1H), 6.28 (d, J=2.0 Hz, 1H), 4.36-4.20 (m, 1H), 3.91 (s, 3H), 3.79-3.40 (m, 4H), 3.16-3.01 (m, 4H), 2.64-2.37 (m, 2H), 1.93-1.68 (m, 4H), 1.61-1.49 (m, 2H), 1.44 (s, 9H).

Provenance & Evidence