Hydrochloric Acid → HCID 178419163, compound

Participants

Reaction Steps

Under an argon atmosphere, a solution of cerium chloride (8.66 g, 3.0 equivalents) in THF (80 mL) was stirred at room temperature (25° C.) for 30 min. Sodium borohydride (1.37 g, 3.1 equivalents) was added, and the mixture was stirred at room temperature for 1 hr. Then bis(2-methylphenyl)phosphine oxide (2.7 g, 11.72 mmoL) synthesized in Reference Example 9 and lithium aluminum hydride (0.53 g, 1.2 equivalents) were successively added at 5° C., and the mixture was stirred at room temperature for 4 hrs. Toluene (80 mL) was added at 3° C., and then 3M—HCl (30 mL) was added. The mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned, and the aqueous layer was extracted with toluene (20 mL). The combined organic layer was washed with 5% aqueous NaCl solution (20 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered by gravity, and the filtrate was concentrated under reduced pressure. Toluene (20 mL) and silica gel (10 g) were added to the residue and the mixture was stirred at room temperature for 10 min. The mixture was filtered by gravity, and the filtrate was concentrated under reduced pressure. THF (5 mL) and BH3.THF (5 mL) were added to the residue at 5° C., and the mixture was stirred at room temperature for 1 hr. The mixture was concentrated under reduced pressure and the residue was recrystallized from heptane to give the title compound (1.15 g, white crystals). yield 43.0%. melting point: 78.0° C.

Provenance & Evidence