Hydrochloric Acid → HCID 178419167, compound

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Reaction Steps

Under a nitrogen stream, a solution of cerium chloride (26.40 g, 3.00 equivalents) in THF (220 mL) was stirred at room temperature (25° C.) for 30 min. Sodium borohydride (4.06 g, 3.00 equivalents) was added, and the mixture was stirred at room temperature for 1.5 hrs. Then bis(m-tolyl)phosphine oxide (8.22 g, 35.7 mmol) synthesized in Reference Example 17 and lithium aluminum hydride (2.06 g, 1.22 equivalents) were successively added at −9° C. and the mixture was stirred for 3 hrs. 6M-HCl (33 mL) was added at −3° C., then water (33 mL) was added and toluene (130 mL) was added at 4° C. The mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned, and the organic layer was washed successively with water (50 mL), 10% aqueous NaHCO3 solution (50 mL) and 10% aqueous NaCl solution (50 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered by gravity, and further passed through a membrane filter (0.2 μm) under reduced pressure. A borane-THF complex (36 mL, 1.02 equivalents) was added to the filtrate at around 0° C. and the mixture was stirred at room temperature for 13.5 hrs. A borane-THF complex (6.2 mL, 0.18 equivalent) was further added at room temperature, and the mixture was concentrated under reduced pressure. The residue was recrystallized from n-hexane and dried (reduced pressure, 40° C.) to give the title compound (1.70 g, white powder). yield 21%

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