反应详情

To 3-({4-[(4-acetyl-3-hydroxy-2-methyl-phenylamino)-methyl]-phenyl}-hydroxy-methyl)-benzonitrile (138 mg, 0.36 mmol) in acetonitrile (14 mL) are added 37% aqueous solution of formaldehyde (140 μL) and NaCNBH3 (69 mg, 1.1 mmol). The pH of the mixture is adjusted to approximately 2 by dropwise addition of 1 N HCl over a 15 min period. The reaction was complete after 1.5 h, during which time the pH of the reaction mixture is monitored every 15 min using pH paper and kept at around 2 by addition of 1N HCl. The reaction mixture is quenched into H2O and basified with saturated aqueous NaHCO3. The mixture is extracted with EtOAc (3×), washed with brine, dried over Na2SO4, and concentrated. Obtained is the title compound as a yellow oil (135 mg, 94%). LC-MS (m/e): 399 (M−1).

1. waitthe pH of the reaction mixture is monitored every 15 min
2. customThe reaction mixture is quenched into H2O
3. extractionThe mixture is extracted with EtOAc (3×)
4. washwashed with brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. customObtained