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

HRID 1593607노트

반응식

HRID 1593607 반응식
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

참가 물질

4

반응물 2

HCID 159087Triacetoxyperiodinane2회HCID 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-cd53a95173c14b25a8103823a30b658d
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297704B2

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