Acetic Acid → HCID 66701315, compound

Participants

Reaction Steps

At RT, 898 μl of a 1-molar solution of sodium cyanoborohydride in tetrahydrofuran were added to a solution of 94 mg (0.20 mmol) of 5-(4-ethylphenyl)-N-phenyl-1-(piperazin-1-ylcarbonyl)piperidine-3-carboxamide, 241 μl (1.20 mmol, 6 eq.) of [(1-ethoxycyclopropyl)oxy](trimethyl)silane, 35 μl (0.62 mmol, 3.1 eq.) of acetic acid and 115 mg of molecular sieves (4 {acute over (Å)}) in 1 ml of methanol. The reaction mixture was stirred under reflux for 5 h and then filtered and adjusted to pH 8 using a 0.2-molar sodium hydroxide solution. After addition of water/dichloromethane and phase separation, the aqueous phase was extracted twice with dichloromethane. The combined organic phases were dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude product was purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 60 mg (65% of theory)

Provenance & Evidence