Tetrabutylammonium Fluoride → Di-tert-butyl (1S,2S,5R,6S)-2-[(tert-butoxycarbonyl)amino]bicyclo[3.1.0]hex-3-ene-2,6-dicarboxylate

HRID 2172987Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2172987
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([NH:26][C@@:27]1([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:32][C@H:31](OS(C)(=O)=O)[C@@H:30]2[C@H:28]1[C@H:29]2[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:25])([CH3:22])([CH3:21])[CH3:20]>O1CCCC1.O>[C:19]([O:23][C:24]([NH:26][C@@:27]1([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH:32]=[CH:31][C@@H:30]2[C@H:28]1[C@H:29]2[C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])=[O:25])([CH3:22])([CH3:20])[CH3:21]

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 86695971HCID 86695971, Verbindung

Produkt 1

HCID 71681345Di-tert-butyl (1S,2S,5R,6S)-2-[(tert-butoxycarbonyl)amino]bicyclo[3.1.0]hex-3-ene-2,6-dicarboxylateAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Add 1M tetrabutylammonium fluoride in tetrahydrofuran (3.84 mL, 3.84 mmol) to di-tert-butyl (1S,2S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (600.00 mg, 1.22 mmol) in tetrahydrofuran (2.03 mL) and heat at reflux for 3 hours. The reaction is then cooled to room temperature, diluted with water, and extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by flash chromatography eluting with 5-75% ethyl acetate in hexanes to give the title compound (0.23 g, 0.58 mmol, 48%).

Aufarbeitung

  1. temperatureheat
  2. temperatureat reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue
  9. customThe residue is purified by flash chromatography
  10. washeluting with 5-75% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f31df39bb429447aaeab2ee101695153
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056844B2

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