Lithium aluminum hydride → {8-amino-1,4-dioxaspiro[4.5]decan-8-yl}methanol

HRID 712108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712108
[AlH4-].[Li+].[NH2:3][C:4]1([C:14](O)=[O:15])[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1>O1CCCC1>[NH2:3][C:4]1([CH2:14][OH:15])[CH2:13][CH2:12][C:7]2([O:8][CH2:9][CH2:10][O:11]2)[CH2:6][CH2:5]1

Komponenten

4

Edukt 2

HCID 28112Lithium aluminum hydrideHCID 70155058-amino-1,4-dioxaspiro[4.5]decane-8-carboxylic Acid

Produkt 1

HCID 84071995{8-amino-1,4-dioxaspiro[4.5]decan-8-yl}methanolAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Lithium tetrahydroaluminate (189 mg, 4.97 mmol) was added in portions to a solution of 8-amino-1,4-dioxaspiro[4.5]decane-8-carboxylic acid (from Aldrich, 0.50 g, 2.5 mmol) in tetrahydrofuran (20 mL) with stirring at about 0° C. The resulting mixture was slowly warmed to room temperature and stirred overnight. Fieser workup (0.2 mL H2O, 0.2 mL 10% NaOH, 0.6 mL H2O) was performed followed by filtration through Celite and concentrated to give 0.41 g of the desired product to be used without further purifications. LCMS calculated for C9H18NO3 (M+H)+: m/z=188.1. Found: 188.0.

Aufarbeitung

  1. temperatureThe resulting mixture was slowly warmed to room temperature
  2. stirringstirred overnight
  3. filtrationFieser workup (0.2 mL H2O, 0.2 mL 10% NaOH, 0.6 mL H2O) was performed followed by filtration through Celite
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c77cc72a3e2546c08e456991be82957a
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181271B2

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