Methanol → 1-[(1-Benzhydryl-azetidin-3-yl)-methoxy-methyl]-5-fluoro-1H-indole

HRID 2056371

Reaktionsgleichung

Reaktionsgleichung von HRID 2056371
[CH:1]([N:14]1[CH2:17][CH:16]([CH2:18]C=O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][CH:26]=[CH:25]2.[OH-:31].[Na+].[CH3:33]O>>[CH:1]([N:14]1[CH2:15][CH:16]([CH:18]([O:31][CH3:33])[N:27]2[C:28]3[C:24](=[CH:23][C:22]([F:21])=[CH:30][CH:29]=3)[CH:25]=[CH:26]2)[CH2:17]1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

5

Edukt 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 678615-FluoroindoleHCID 58739272(1-Benzhydryl-azetidin-3-yl)-acetaldehyde

Produkt 1

HCID 218920451-[(1-Benzhydryl-azetidin-3-yl)-methoxy-methyl]-5-fluoro-1H-indoleAusbeute 56 %

Versuchsvorschrift

A solution of (1-benzhydryl-azetidin-3-yl)-acetaldehyde (0.30 g, 1.2 mmol), 5-fluoroindole (0.8 g, 6.0 mmol) and sodium hydroxide (0.06 g, 1.6 mmol) in methanol (20 mL) was refluxed for 6 hours. The reaction was quenched with water and extracted with methylene chloride (3×100 mL). The organic layer was washed with water (3×80 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The crude oil was column chromatographed on silica gel (30-40% ethyl acetate/hexane). The product-containing fractions were concentrated under vacuum to give 0.27 g (56%) of the title compound as a light yellow oil. 1H NMR (500 MHz, DMSO-D6): δ 2.62 (t, J=6.4 Hz, 1 H), 2.90-2.95 (m, 2 H), 3.02 (t, J=6.1 Hz, 1 H), 3.09 (s, 3 H), 3.26-3.31 (m, 1 H), 4.40 (br, 1 H), 4.58 (d, J=8.8 Hz, 1 H), 6.89 (m, 1 H), 7.13-7.18 (m, 2 H), 7.22-7.27 (m, 4 H), 7.31-7.39 (m, 7 H), 11.10 (br, 1 H).

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionextracted with methylene chloride (3×100 mL)
  3. washThe organic layer was washed with water (3×80 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customchromatographed on silica gel (30-40% ethyl acetate/hexane)
  8. concentrationThe product-containing fractions were concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1f5d6b5d4fbc4015bcf928e93c079cc7
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335666B2

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