Water → 2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

HRID 2404968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2404968
[NH2:1][C@H:2]1[C@@H:6]2[O:7][C:8]([CH3:11])([CH3:10])[O:9][C@@H:5]2[C@@H:4]([O:12][CH2:13][C:14](OCC)=[O:15])[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[NH2:1][C@H:2]1[C@@H:6]2[O:7][C:8]([CH3:10])([CH3:11])[O:9][C@@H:5]2[C@@H:4]([O:12][CH2:13][CH2:14][OH:15])[CH2:3]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 70854858ethyl 2-{[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]oxy}acetate

Produkt 1

HCID 99425962-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanolAusbeute 65,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of ethyl 2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)acetate (4.2 g, 16.2 mmol, 1.00 equiv.) in dry tetrahydrofuran (50 mL) was slowly added to a suspension of lithium aluminum hydride (1.23 g, 32.4 mmol, 2.00 equiv.) in tetrahydrofuran (50 mL). The mixture was heated at reflux for about 1 hour, and then water was added (2 mL). After the solids were collected by filtration, the solids were washed with tetrahydrofuran (50 mL) and then dried in vacuo to give the title product as a yellow oil (2.3 g, 65%). MS: m/z=218 (MH)+.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for about 1 hour
  3. filtrationAfter the solids were collected by filtration
  4. washthe solids were washed with tetrahydrofuran (50 mL)
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cca83917731c4ae88525fa2e19200126
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802850B2

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