Potassium Sodium Tartrate → Spiro[cyclobutane-1,3'-indoline]

HRID 1178915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178915
[H-].[H-].[H-].[H-].[Li+].[Al+3].F[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1([C:20]#[N:21])[CH2:19][CH2:18]OC[CH2:15]1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(COC)OC>[NH:21]1[C:8]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:14]2([CH2:15][CH2:18][CH2:19]2)[CH2:20]1

Komponenten

5

Edukt 3

HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 49875771HCID 49875771, Verbindung

Produkt 1

HCID 27274706Spiro[cyclobutane-1,3'-indoline]Ausbeute 10,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Add LiAlH4 (266 mg, 7.01 mmol) to a solution of 4-(2-fluoro-phenyl)-tetrahydro-pyran-4-carbonitrile (488 mg, 2.72 mmol) in dimethoxyethane (30 mL). Stir the solution at reflux for 4d, then add aq. Satd Rochelle's salt solution (30 mL) and stir for an additional 1 h at RT. Extract the mixture with Et2O (3×30 mL). Combine the organic extracts and wash with brine (30 mL). Dry, filter and concentrate the organic solution then purify the crude material by flash chromatography, using a linear gradient of 100% hexanes to 30% EtOAc/hexanes, to give the title compound (44 mg, 10%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.31 (m, 1H), 7.03 (dt, 1H, J=1.4, 7.5), 6.79 (dt, 1H, J=0.9, 7.5), 6.64 (d, 1H, J=7.9), 2.36 (m, 2H), 2.21 (m, 2H), 2.02 (m, 2H).

Aufarbeitung

  1. extractionExtract the mixture with Et2O (3×30 mL)
  2. washCombine the organic extracts and wash with brine (30 mL)
  3. customDry
  4. filtrationfilter
  5. concentrationconcentrate the organic solution
  6. customthen purify the crude material by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-95074c86e1374019a4af3777d047cf35
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276516B2

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