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Hydrochloric Acid → 6-Hydroxymethyl-8-benzyl-8-azaspiro[4,5]decane

HRID 1815826
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1815826
C[O:2][C:3]([CH:5]1[CH2:14][N:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:11][C:6]21[CH2:10][CH2:9][CH2:8][CH2:7]2)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[OH:2][CH2:3][CH:5]1[CH2:14][N:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:11][C:6]21[CH2:10][CH2:9][CH2:8][CH2:7]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 697452468-Benzyl-8-azaspiro[4,5]decane-6-carboxylic acid methyl ester

Produkt 1

HCID 224957566-Hydroxymethyl-8-benzyl-8-azaspiro[4,5]decane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 11.4 gm (39.1 mMol) 8-benzyl-8-azaspiro[4,5]decane-6-carboxylic acid methyl ester in 150 mL tetrahydrofuran was treated dropwise with a solution of 58 mL (58 mMol) lithium aluminum hydride (1.0 M in tetrahydrofuran). The reaction mixture was heated at reflux for 4 hours and was then cooled in an ice bath. The mixture was then diluted with ethyl acetate and treated dropwise with 100 mL 1N hydrochloric acid. The pH of the solution was then adjusted to about 8 with 5N sodium hydroxide and the mixture was extracted well with dichloromethane. The organic phases were combined, dried over magnesium sulfate and concentrated under reduced pressure to provide 6-hydroxymethyl-8-benzyl-8-azaspiro[4,5]decane.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hours
  3. temperaturewas then cooled in an ice bath
  4. extractionthe mixture was extracted well with dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-78e94dc9ad2b4c5b8570767195a66795
Quelldatensatz
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06881733B1

Notizen zur Reaktion

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