Cyclohexene → Oseltamivir

HRID 991268

Reaktionsgleichung

Reaktionsgleichung von HRID 991268
[C:1]([NH:4][C@@H:5]1[C@@H:10]([N:11]=[N+]=[N-])[CH2:9][C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7][C@H:6]1[O:19][CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])(=[O:3])[CH3:2].C1CCCCC=1>C(O)C.[Ni]>[C:1]([NH:4][C@@H:5]1[C@@H:10]([NH2:11])[CH2:9][C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7][C@H:6]1[O:19][CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 8079CyclohexeneHCID 9967681Ethyl (3R,4R,5S)-4-acetamido-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

Produkt 1

HCID 65028Oseltamivir

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

100 g (0.295 mol) ethyl (3R, 4R, 5S)-4-acetamido-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate were dissolved in 800 ml ethanol and placed in a 21 steel autoclave together with 34 g Raney Nickel (Degussa) in 200 ml ethanol. The autoclave was closed rinsed twice with nitrogen and then set under 2 bar hydrogen pressure. Hydrogenation took place at a temperature of 20-25° C. under mechanical stirring a 1000 rpm until, after all the starting material had reacted, also the content of the “2-azido-5-amino intermediate” was ≦0.01% area (GC measurement) which was about 5-8 h. However, it was found that due to this “overhydrogenation” the “cyclohexene double bond” became hydrogenated, too.

Aufarbeitung

  1. customThe autoclave was closed
  2. washrinsed twice with nitrogen
  3. customat a temperature of 20-25° C.
  4. customhad reacted

Quellen und Nachweise

ORD-Eintrag
ord-a52e8e15df294d5089e7e3f7528627d8
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06462226B1

Verknüpfte Notizen

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