Ammonia → (5S,6R)-6-amino-2,2-dimethyl-1,3-dioxepan-5-ol

HRID 1904067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1904067
[CH3:1][C:2]1([CH3:10])[O:9][CH2:8][CH:7]2[CH:5]([O:6]2)[CH2:4][O:3]1.O.[NH3:12]>>[CH3:1][C:2]1([CH3:10])[O:9][CH2:8][C@@H:7]([NH2:12])[C@H:5]([OH:6])[CH2:4][O:3]1

Komponenten

4

Edukt 3

HCID 222Ammonia2×HCID 962WaterHCID 110947474,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

Produkt 1

HCID 58287017(5S,6R)-6-amino-2,2-dimethyl-1,3-dioxepan-5-olAusbeute 87 %

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

A steel bomb was charged with liquid ammonia (60 ml) with cooling in an isopropanol-dry ice bath maintained at -70° C. The epoxide (III) (21.46 g, 0.15 mole) was added to it, followed by water (2.70 ml, 0.15 mole). The bomb was sealed and, then, heated in an oil bath at 120° for 4 hr. The bomb was cooled, opened and the ammonia was allowed to evaporate. The crude residue was triturated with ether, chilled, and the crystalline product was isolated by filtration. The amine (IV) was obtained as white prisms. (18.78 g, yield 87%). m.p. 81.5°-82.5°.

Aufarbeitung

  1. temperaturewith cooling in an isopropanol-dry ice bath
  2. customThe bomb was sealed
  3. temperatureheated in an oil bath at 120° for 4 hr
  4. temperatureThe bomb was cooled
  5. customto evaporate
  6. customThe crude residue was triturated with ether
  7. temperaturechilled
  8. customthe crystalline product was isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-db2f99143d6546f2bcb9e11aace1ff70
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04439613

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