Trifluoroacetic acid → 7-Benzyl-1-cyano-2-oxa-7-azabicyclo[3.3.0]octane

HRID 1900228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900228
[O:1]1[CH2:5][CH2:4][CH:3]=[C:2]1[C:6]#[N:7].C(N(CC)CC)C.FC(F)(F)C(O)=O.[CH2:22]([N:29]([CH2:35]OC)[CH2:30][Si](C)(C)C)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([N:29]1[CH2:30][C:2]2([C:6]#[N:7])[CH:3]([CH2:4][CH2:5][O:1]2)[CH2:35]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 136240424,5-Dihydrofuran-2-carbonitrile

Produkt 1

HCID 217047477-Benzyl-1-cyano-2-oxa-7-azabicyclo[3.3.0]octane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

14.4 g (0.15 mol) of 4,5-dihydrofuran-2-carbonitrile are introduced in 300 ml of absolute methylene chloride, 1.8 g of triethylamine and 1.8 g of trifluoroacetic acid are added, and the mixture is warmed to 40° C. 42.6 g (0.15 mol) of N-benzyl-N-methoxymethyl-N-trimethylsilylmethylamine are added dropwise to this mixture which is then stirred at 40° C. for 15 hours. It is then washed with 50 ml of saturated sodium hydrogen carbonate solution, dried over MgSO4, concentrated and distilled twice.

Aufarbeitung

  1. washIt is then washed with 50 ml of saturated sodium hydrogen carbonate solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. distillationdistilled twice

Quellen und Nachweise

ORD-Eintrag
ord-ee1860aab4bf4ac7beec01d2054018d8
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05574161

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