Sodium Sulfite → 2-(2,3-Dihydroxypropyl)-6-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonitrile

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Reaction Steps

Compound 88 (261 mg, 0.83 mmol) was dissolved in 24 mL of acetone and 10 mL of water. OsO4 (Aldrich, 2.5% in 2-Me-2-propanol, 1.04 mL) was added then NMO (116 mg, 1 mmol). The resulting mixture was stir at RT overnight then diluted with 1:1 sat NaHCO3/sat Na2SO3. It was partitioned between EtOAc and aq NaHCO3, then the organic phase was washed once with brine. The combined aqueous phases were washed once with EtOAc. Drying (Na2SO4) and concentration gave the title compound 89 as a light brown solid.

Provenance & Evidence