Carbon Dioxide → 8-ethyl-8-azabicyclo[3.2.1]octan-3-one

HRID 648192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 648192
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)[O:4]1.Cl.C(C(O)=O)[C:12]([CH2:14][C:15](O)=O)=O.C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O.[Na+].[Na+].[Na+].[CH2:37]([NH2:39])[CH3:38].C(=O)=O>O>[CH2:37]([N:39]1[CH:6]2[CH2:5][CH2:12][CH:14]1[CH2:15][C:3](=[O:4])[CH2:7]2)[CH3:38]

Komponenten

8

Edukt 6

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 6224Trisodium citrateHCID 6341EthylamineHCID 68328Acetonedicarboxylic acidHCID 790982,5-Dimethoxytetrahydrofuran

Produkt 1

HCID 2729578-ethyl-8-azabicyclo[3.2.1]octan-3-oneAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel3×

Versuchsvorschrift

52 ml of 2,5-dimethoxy-tetrahydrofuran (0.402 moles) are dissolved in 58 ml of water and acidified with 1.2 ml of 37% hydrochloric acid. After 15 minutes, 58 g of acetonedicarboxylic acid (0.397 moles) are added followed by 40.4 g of tribasic sodium citrate bihydrate (0.137 moles) dissolved in 58 ml of water. 18.5 g of ethylamine (0.411 moles) in 35 ml of water are then dripped in. The mixture is left stirring until carbon dioxide ceases to be evolved. It is then saturated with K2CO3 and extracted with ethyl ether. After drying and evaporating the solvent, the crude product is distilled under vacuum. 27.9 g of 8-ethyl-8-azabicyclo-[3.2.1]-octan-3-one are obtained.

Aufarbeitung

  1. waitThe mixture is left
  2. extractionsaturated with K2CO3 and extracted with ethyl ether
  3. customAfter drying
  4. customevaporating the solvent
  5. distillationthe crude product is distilled under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d7fc5ef1874843058f1260b1529652ea
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04411902

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