Water → (8-Phenyl-1,4-dioxaspiro[4.5]decan-8-YL)methanamine

HRID 1477187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1477187
[C:1]1([C:7]2([C:17]#[N:18])[CH2:16][CH2:15][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:1]1([C:7]2([CH2:17][NH2:18])[CH2:8][CH2:9][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:15][CH2:16]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 122302748-Phenyl-1,4-dioxaspiro[4.5]decane-8-carbonitrileHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 20596179(8-Phenyl-1,4-dioxaspiro[4.5]decan-8-YL)methanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel4×

Versuchsvorschrift

A solution of the title compound of step 3 (10.0 g, 41.1 mmol) in dry THF (70 mL) was slowly added to a mixture of LiAlH4 (1.87 g, 49.3 mmol) in dry THF (25 mL) in a protective gas. The mixture was then stirred for 3 h with reflux. After the reaction mixture had cooled, a solution of water (1.87 mL, 104 mmol) diluted with a little THF was added in drops with ice cooling and subsequently stirred for 10 min. 15% aqueous NaOH (1.87 mL, 8.17 mmol) diluted with a little THF was then added in drops and water (5.6 mL) was then added again. The precipitate formed was filtered over diatomaceous earth and the solvent removed in a vacuum. The amine remained as residue.

Aufarbeitung

  1. temperaturewith reflux
  2. temperatureAfter the reaction mixture had cooled
  3. additionwas added in drops with ice cooling
  4. stirringsubsequently stirred for 10 min
  5. additionwas then added again
  6. customThe precipitate formed
  7. filtrationwas filtered over diatomaceous earth
  8. customthe solvent removed in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e5d3bf51995f49cba3a121aa45c4136c
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403767B2

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