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

HRID 1727396Notes

Reaction equation

HRID 1727396 reaction equation
[N+:1]([C:4]1[CH2:16][O:15][C:14]2[CH:13]=[CH:12][C:11]3[CH2:10][NH:9][C:8](=[O:17])[C:7]=3[C:6]=2[CH:5]=1)([O-:3])=[O:2].[Na]>>[N+:1]([CH:4]1[CH2:16][O:15][C:14]2[CH:13]=[CH:12][C:11]3[CH2:10][NH:9][C:8](=[O:17])[C:7]=3[C:6]=2[CH2:5]1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 5360545SodiumHCID 575676868-nitro-2,3-dihydropyrano[3,2-e]isoindol-1(7H)-one

Product 1

HCID 575676678-nitro-2,3,8,9-tetrahydropyrano[3,2-e]isoindol-1(7H)-oneYield 71.2%

Procedure

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.

Workup

  1. customResulting mixture
  2. filtrationThe silica gel was filtered
  3. washwashed well with CHCl3
  4. washThe filtrate was washed with H2O
  5. customThe organic solution was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89248bfa0eec418b8cdd16fb7a42dcd1
Source dataset
uspto-grants-2009_02
Patent number
US07495111B2

Reaction notes

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