Hydrochloric Acid → 2-(4-Cyclopropyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 1942215

Reaktionsgleichung

Reaktionsgleichung von HRID 1942215
C(O[C:4]([C:6]1([CH2:19][CH2:20]OC)[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1)=[O:5])C.[CH:23]1([C:26]2[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=2)[CH2:25][CH2:24]1.[Cl-].C[Al+]C.Cl>C1(C)C=CC=CC=1>[CH:23]1([C:26]2[CH:32]=[CH:31][C:29]([N:30]3[CH2:20][CH2:19][C:6]4([CH2:7][CH2:8][NH:9][CH2:10][CH2:11]4)[C:4]3=[O:5])=[CH:28][CH:27]=2)[CH2:25][CH2:24]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 122539274-CyclopropylanilineHCID 16686359Dimethylalumanylium chlorideHCID 582872614-(2-Methoxy-ethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

Produkt 1

HCID 582872772-(4-Cyclopropyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A mixture of 1.3 g (4.1 mmol) 4-(2-Methoxy-ethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester, 0.604 g (4.5 mmol) 4-cyclopropylaniline and 8.24 mL (8.24 mmol) dimethylaluminum chloride (1N in hexane) in 100 mL toluene was stirred at 115° C. for 15 h. After cooling to room temperature the mixture was poured into ice, the mixture was acidified with HCl aq. to pH=2 and extracted with ethyl acetate. The aqueous layer was basified with NaOH pellets to pH=8 and extracted with DCM. The combined organic layers were dried with MgSO4 and evaporated to dryness. The residue was purified by column chromatography on silica (amine) with a gradient formed from ethyl acetate and methanol to yield after evaporation of the product containing fractions 0.468 g (42%) of the title compound as light yellow solid. MS m/e: 270.0 [M+H]+.

Aufarbeitung

  1. temperatureAfter cooling to room temperature the mixture
  2. additionwas poured into ice
  3. extractionextracted with ethyl acetate
  4. extractionextracted with DCM
  5. dry with materialThe combined organic layers were dried with MgSO4
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography on silica (amine) with a gradient
  8. customformed from ethyl acetate and methanol
  9. customto yield
  10. customafter evaporation of the product
  11. additioncontaining fractions 0.468 g (42%) of the title compound as light yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-f0b6a5a0714b42829f5416cad43f52cd
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389539B2

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