Ethanol → Ethyl-4-(spiro[indene-1,4'-piperidine]-1'-ylmethyl)benzoate

HRID 390392

Reaktionsgleichung

Reaktionsgleichung von HRID 390392
Br[CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][CH:4]=1.C([N:17]([CH:20]([CH3:22])C)[CH2:18][CH3:19])(C)C.[CH2:23](O)[CH3:24]>>[CH2:10]([O:9][C:7](=[O:8])[C:6]1[CH:12]=[CH:13][C:3]([CH2:2][N:17]2[CH2:18][CH2:19][C:23]3([C:24]4[C:5](=[CH:4][CH:3]=[CH:13][CH:12]=4)[CH:6]=[CH:7]3)[CH2:22][CH2:20]2)=[CH:4][CH:5]=1)[CH3:11]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 954261Ethyl 4-(bromomethyl)benzoate

Produkt 1

HCID 58230576Ethyl-4-(spiro[indene-1,4'-piperidine]-1'-ylmethyl)benzoateAusbeute 60 %

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of spiro-[indene-1,4-piperidine]trifluoroacetate (4 g, 14 mmol) in ethanol (25 mL) is added ethyl 4-(bromomethyl)-benzoate (2.9 g, 12.6 mmol), followed by diisopropylethylamine (9.6 mL, 56 mmol). The reaction mixture is refluxed at 85° C. for overnight. The ethanol is removed under reduced pressure and the residue is partitioned between EtOAc (150 mL) and water (50 mL). The organic layer is washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel chromatography, eluting with hexane:ethyl acetate (8.0:2.0) to give the title compound as brown solid (2.8 g, 60%). 1H NMR (400 MHz) 7.94 (d, J=8 Hz, 2H), 7.51 (d, J=8 Hz, 2H), 7.43 (d, J=7.2 Hz, 1H), 7.31 (d, J=7.2 Hz, 1H), 7.18 (m, J=7.2 Hz, 2H), 6.94 (d, J=5.6 Hz, 1H), 6.78 (d, J=5.6 Hz, 1H), 4.30 (q, J=7.2 Hz, 2H), 3.67 (s, 2H), 2.85 (d, J=11.6 Hz, 2H), 2.38 (t, J=11.6 Hz, 2H), 2.09 (t, J=10.4 Hz, 2H), 1.31 (t, J=7.2 Hz, 2H), 1.19 (d, J=12.8 Hz, 2H).

Aufarbeitung

  1. customThe ethanol is removed under reduced pressure
  2. customthe residue is partitioned between EtOAc (150 mL) and water (50 mL)
  3. washThe organic layer is washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with hexane:ethyl acetate (8.0:2.0)

Quellen und Nachweise

ORD-Eintrag
ord-6c4aa83c8d2c4cffbab02671451f0b35
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383642B2

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