Sodium Bicarbonate → HCID 67419126, compound

Participants

Reaction Steps

In a round-bottom flask, 715 mg (2.74 mmol) of 12 was dissolved in 10 mL CH3COOH and 5 mL of H2O. To this mixture was added 50 mg of 10% Pd on carbon, and the suspension was heated and stirred at reflux for 12 h. The mixture was cooled, filtered, and the solvents evaporated under reduced pressure. To the residue was added 20 mL of conc. NaHCO3, and this mixture was extracted thoroughly with EtOAc. The pooled organic extracts were washed once with brine, dried over MgSO4, and the solvents removed under reduced pressure to yield 605 mg of an orange oil that was pure (2R,5S)-1-(3-methoxyphenyl)-2,5-dimethylpiperazinium acetate by NMR. 1H NMR (CDCl3) δ 7.21 (t, 1H), 6.73 (dd, 1H), 6.62 (m, 1H), 6.67 (m, 1H), 6.63 (m, 1H), 3.79 (s, 3H), 3.12-2.90 (m, 4H), 2.70 (dd, 1H), 2.46 (dd, 1H), 1.07 (d, 3H), 0.93 (d, 3H). ESIMS: m/z 221 (M+H+, 100). General procedure c. was employed using 363 mg (1.65 mmol) of this oil affording a residue that was dissolved in 5 mL of MeOH and stirred over excess NaHCO3. The mixture was filtered, and the solvents subjected to rotary evaporation to afford a residue that was purified by chromatography affording 215 mg of 13 as a white solid (63% yield). Spectral information for this compound was found to be identical to 17.

Provenance & Evidence