Trifluoroacetic acid → 1-Oxa-9-azaspiro[5.5]undec-2-en-4-one

HRID 1478427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478427
[O:1]=[C:2]1[CH:19]=[CH:18][O:17][C:4]2([CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]2)[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:9]1[C:4]2([O:17][CH:18]=[CH:19][C:2](=[O:1])[CH2:3]2)[CH2:5][CH2:6][NH:7][CH2:8]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 897085271-Oxa-9-azaspiro[5.5]undec-2-ene-9-carboxylic acid, 4-oxo-, 1,1-dimethylethyl ester

Produkt 1

HCID 897083431-Oxa-9-azaspiro[5.5]undec-2-en-4-oneAusbeute 239,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 8-oxo-11-oxa-3-azaspiro[5.5]undec-9-ene-3-carboxylate (200 mg, 0.748 mmol) in CH2Cl2 (2.4 mL) was added TFA (0.6 mL, 7.8 mmol). The mixture was stirred at room temperature for 15 min. Solvent was removed. The crude material was evaporated again from toluene (2×) and dried under high vacuum overnight to provide 11-oxa-3-azaspiro[5.5]undec-9-en-8-one (300 mg). 1H NMR (400 MHz, CDCl3) δ 7.34 (d, J=6.1 Hz, 1H), 5.57 (d, J=6.1 Hz, 1H), 3.45 (d, J=11.7 Hz, 2H), 3.34 (dd, J=24.1, 12.7 Hz, 2H), 2.67 (s, 2H), 2.38 (d, J=14.6 Hz, 2H), 1.98 (td, J=14.8, 4.8 Hz, 2H). ESI-MS m/z calc. 167.09, found 168.2 (M+1)+; Retention time: 0.17 minutes (3 minute run).

Aufarbeitung

  1. customSolvent was removed
  2. customThe crude material was evaporated again from toluene (2×)
  3. customdried under high vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-c23f8b9a0961458fa39b640b967e6802
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403839B2

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