Triacetoxyperiodinane → 6-Fluoro-2,3,4,9-tetrahydro-1H-carbazole-3-carbaldehyde

HRID 1593607Notes

Reaction equation

HRID 1593607 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)[O:14][C:12](=O)[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)=O.[F:23][C:24]1[CH:25]=[C:26]2[C:34](=[CH:35][CH:36]=1)[NH:33]C1CC(C(NC[C@@H]3OC4=C5C(=CC=C4OC3)N=C(C)C=C5)=O)CCC2=1>ClCCl>[F:23][C:24]1[CH:36]=[C:35]2[C:34](=[CH:26][CH:25]=1)[NH:33][C:8]1[CH2:7][CH2:6][CH:11]([CH:12]=[O:14])[CH2:10][C:9]2=1

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 866076466-fluoro-N-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}-2,3,4,9-tetrahydro-1H-carbazole-2-carboxamide

Product 1

HCID 251395066-Fluoro-2,3,4,9-tetrahydro-1H-carbazole-3-carbaldehydeYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (7.37 g, 17.4 mmol) was added portion-wise to a stirred solution/suspension of alcohol II (2.64 g, 11.8 mmole) in dichloromethane (120 mL). The alcohol completely dissolved after the Dess-Martin reagent was added. The reaction mixture was stirred at ambient temperature for 30 min, and then quenched with ethanol. The reaction mixture was diluted with ether (860 mL) and washed twice with saturated aqueous sodium bicarbonate (550 mL) followed by 5% sodium thiosulfate pentahydrate. After washing with brine and drying (MgSO4), the solvent was evaporated to give a residue which was purified by chromatography on silica gel eluting with hexane/ethyl acetate (4:1). Compound V was obtained in 47% yield (1.2 g). mp: 96-98° C. MS: [M−H]− @m/z=216.1.

Workup

  1. additionwas added
  2. customquenched with ethanol
  3. additionThe reaction mixture was diluted with ether (860 mL)
  4. washwashed twice with saturated aqueous sodium bicarbonate (550 mL)
  5. washAfter washing with brine
  6. dry with materialdrying (MgSO4)
  7. customthe solvent was evaporated
  8. customto give a residue which
  9. customwas purified by chromatography on silica gel eluting with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-cd53a95173c14b25a8103823a30b658d
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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