Sodium Perborate → HCID 117802896, compound

HRID 520315Notes

Reaction equation

HRID 520315 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:7]2.B(O[O-])=[O:30].[Na+]>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([OH:30])[CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 517072Sodium PerborateHCID 131735494HCID 131735494, compound

Product 1

HCID 117802896HCID 117802896, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 144g (16.0 g, 40.9 mmol) in THF (200 mL) and H2O (200 mL) was added sodium perborate (26.4 g, 171.8 mmol) in one portion at RT under N2. See FIG. 3. The mixture was stirred at room temperature for 8 h. The mixture was filtered and the filtration was extracted with EtOAc (400 mL×5). The combined organic phase was washed with saturated brine (200 mL×2), dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (PE/EA=30/1, 5/1) to afford 9.50 g (82.6%) of tert-butyl 8-fluoro-6-hydroxy-1-oxo-3,4-dihydroisoquinoline-2(1H)-carboxylate 144h. 1H NMR (400 MHz, CDCl3) δ 6.56-6.60 (d, J=13.6 Hz, 1H), 6.49 (s, 1H), 3.83-3.86 (m, 2H), 2.82-2.84 (m, 2H), 1.49 (s, 9H), 1.20 (s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. filtrationthe filtration
  3. extractionwas extracted with EtOAc (400 mL×5)
  4. washThe combined organic phase was washed with saturated brine (200 mL×2)
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (PE/EA=30/1, 5/1)

Sources & evidence

ORD record
ord-fd6fbfebd6eb42b38a4075ac973a9296
Source dataset
uspto-grants-2016_05
Patent number
US09326985B2

Reaction notes

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