Water → 2-Azaspiro[4.5]decane-3,8-dione

HRID 2099692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2099692
O1[C:5]2([CH2:15][CH2:14][C:8]3([CH2:12][C:11](=[O:13])[NH:10][CH2:9]3)[CH2:7][CH2:6]2)[O:4]CC1.O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O>[CH2:9]1[C:8]2([CH2:7][CH2:6][C:5](=[O:4])[CH2:15][CH2:14]2)[CH2:12][C:11](=[O:13])[NH:10]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 577954141,4-Dioxa-10-azadispiro[4.2.4^{8}.2^{5}]tetradecan-11-one

Produkt 1

HCID 577955102-Azaspiro[4.5]decane-3,8-dioneAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-11-one (3.95 g, 18.7 mmol) in 160 mL of acetone was added 16 mL of water and pyridinium p-toluenesulfonate (1.41 g, 5.61 mmol). The resulting mixture was stirred at reflux for 20 h. Then, it was cooled and concentrated. The crude was purified by silica gel column chromatography using a 5% MeOH:EtOAc mixture as eluent to afford 2-aza-spiro[4.5]decane-3,8-dione (1.80 g, 58%) as a white solid.

Aufarbeitung

  1. temperatureat reflux for 20 h
  2. temperatureThen, it was cooled
  3. concentrationconcentrated
  4. customThe crude was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ec403a407a7e4a1c9372b04caef70c72
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569600B2

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