Sodium borohydride → HCID 86610858, compound

Participants

Reaction Steps

A solution of 2.5% w/v osmium tetroxide in tert-butanol (0.47 ml) was added to a vigorously stirred solution of 4-chloro-6-(pent-3-en-1-yl)-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}pyrimidine (prepared as described in Example 34) in THF (10.5 ml) and water (2.8 ml). Solid sodium periodate (951 mg, 4.44 mmol) was then added. The reaction was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried (Na2SO4), and the solvent removed by evaporation. The residue was dissolved in THF (13.5 ml) and distilled water (5.0 ml) and sodium borohydride (59 mg, 1.59 mmol) was added. The reaction was stirred at ambient temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and water and the layers partitioned and separated. The ethyl acetate layer was washed with water and saturated brine, dried (Na2SO4) and the solvent removed by evaporation. The residue was purified by flash chromatography on silica gel eluting with methanol/DCM (1.5:98.5) to give the title compound (205 mg, 36%).

Provenance & Evidence