Sodium → 8-nitro-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-one

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Reaction Steps

To 8-nitro-2,3-dihydropyrano[3,2-e]isoindol-1(7H)-one ((70), 1.1 g, 4.74 mmol) in solvent A (CHCl3, 100 ml) and solvent B (i-PrOH 4 ml) was added silica gel (3.3 g), followed by addition of sodium boronhydride (400 mg, 11.5 mmol) in portions. Resulting mixture was stirred for 2 hr. The silica gel was filtered and washed well with CHCl3. The filtrate was washed with H2O, and sat NaCl. The organic solution was separated and dried over Na2SO4 and concentrated in vacuo to give the title compound (790 mg, 71%) as a solid.

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