Trifluoroacetic acid → 3-Methyl-3,9-diazaspiro[5.5]undecane

HRID 548942

Reaktionsgleichung

Reaktionsgleichung von HRID 548942
C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][N:16](C)[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[CH3:6][N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:10][CH2:9]1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 58808179HCID 58808179, Verbindung

Produkt 1

HCID 218132933-Methyl-3,9-diazaspiro[5.5]undecaneAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

9-Methyl-3,9-diaza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (435 mg, 1.62 mmol) was dissolved in dichloromethane (11 mL) and cooled on ice. Trifluoroacetic acid (4 mL) in dichloromethane (5 mL) was added and the reaction mixture was stirred at room temperature for 2 h. Evaporation to dryness, co-evaporation with toluene, ethyl acetate and diethyl ether gave a foam which was dissolved in dichloromethane, and sodium hydroxide (2 N) was added. The aqueous phase was extracted five times with dichloromethane. The combined organic phase was washed with brine, dried (sodium sulfate), filtered and evaporated to give 214 mg (78%) of 3-methyl-3,9-diaza-spiro[5.5]undecane.

Aufarbeitung

  1. temperaturecooled on ice
  2. customEvaporation to dryness, co-evaporation with toluene, ethyl acetate and diethyl ether
  3. customgave a foam which
  4. extractionThe aqueous phase was extracted five times with dichloromethane
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-34833a95099246088d70e08d92898144
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943630B2

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