Triethylamine → 1,1-Dimethylethyl (2S)-4-{[4-(acetylamino)-2-methylphenyl]methyl}-2-methyl-1-piperazinecarboxylate

Participants

Reaction Steps

D5 (326 mg, 1.8 mmol), 1,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate hydrochloride (436 mg, 1.8 mmol), triethylamine (0.282 mL, 2 mmol) and sodium triacetoxyborohydride (781 mg, 3.7 mmol) were stirred together in 1,2-DCE (15 mL) for 17 h. Saturated aqueous NaHCO3 was added and the reaction mixture stirred for 1 h. The organic layer was separated and washed with water and brine, then dried and concentrated. The crude product was purified by chromatography. Elution with 0-100% EtOAc/petroleum ether yielded the title compound as a colourless oil (573 mg). δH (CDCl3, 400 MHz) 7.28 (2H, m), 7.15 (2H, m), 4.17 (1H, br.s), 3.76 (1H, d), 3.36 (2H, s), 3.00 (1H, m), 2.70 (1H, d), 2.56 (1H, d), 2.36 (3H, s), 2.17 (4H, m), 1.95 (1H, m), 1.45 (9H, s), 1.18 (3H, d). MS (ES+): MH+ 362.3.

Provenance & Evidence