1-Acetylpiperazine → tert-Butyl 4-[(4-acetylpiperazin-1-yl)methyl]-6-methoxypyridin-2-ylcarbamate

Participants

Reaction Steps

To a solution of tert-butyl 4-formyl-6-methoxypyridin-2-ylcarbamate (15-3, 292 mg, 1.16 mmole) and 1-acetylpiperazine (178 mg, 1.39 mmole) in 2% glacial HOAc in CH2Cl2 (5 mL) was added NaBH(OAc)3 (270 mg, 1.27 mmole) at RT. After 1.5 hr the mixture was quenched with saturated NaHCO3 and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (gradient, 0-5% EtOH/EtOAc) gave the titled compound as a white foam. 1H-NMR (500 MHz, CDCl3) δ 7.41 (s, 1 H), 7.00 (bs, 1 H), 6.43 (s, 1 H), 3.83 (s, 3 H), 3.63 (bs, 2 H), 3.46 (bs, 4 H), 2.41 (m, 4 H), 2.08 (s, 3 H), 1.52 (s, 9 H); MS (ES) (M+H)+ 365.

Provenance & Evidence