Ammonium Chloride → HCID 67282946, compound

Participants

Reaction Steps

Sodium borohydride (2.15 g) was added to a methanol-THF (20 ml-100 ml) solution of the compound 321-1 (17.4 g), while the solution was stirred under cooling on ice. The obtained mixture was stirred at room temperature for 1 hour. A saturated ammonium chloride aqueous solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The obtained residue was dissolved in dichloromethane (100 ml). Triethylamine (19.8 ml) and methanesulfonyl chloride (8.05 ml) were added to the solution, while the solution was stirred under cooling on ice. The obtained mixture was stirred at room temperature for 14 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The obtained residue was dissolved in acetonitrile (100 ml). Sodium iodide (2.83 g) and sodium cyanide (6.95 g) were added to the solution, and the obtained mixture was stirred at 80° C. for 3 hours. Thereafter, sodium cyanide (9.27 g) and dimethyl sulfoxide (30 ml) were added to the reaction solution, and the obtained mixture was stirred at 100° C. for 5 hours. The reaction solution was concentrated under reduced pressure. Water was added to the residue, and the mixture was then extracted with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride aqueous solution, then dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=1:0 to 1:1), so as to obtain the title compound (11.5 g).

Provenance & Evidence