Triethylamine → HCID 72444859, Verbindung

HRID 1767123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1767123
C(N(CC)CC)C.Cl.[NH2:9][OH:10].[C:11]([C:13]12[N:19]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH:16]([CH2:17][CH2:18]1)[CH2:15][CH2:14]2)#[N:12].[CH3:30][O:31][C:32]([C:34]#[C:35][C:36]([O:38][CH3:39])=[O:37])=[O:33]>CO>[CH3:30][O:31][C:32](=[O:33])[C:34]([O:10][N:9]=[C:11]([NH2:12])[C:13]12[N:19]([C:20]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:21])[CH:16]([CH2:17][CH2:18]1)[CH2:15][CH2:14]2)=[CH:35][C:36]([O:38][CH3:39])=[O:37]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 12980Dimethyl acetylenedicarboxylateHCID 443297Hydroxyamine hydrochlorideHCID 21112384Phenylmethyl 1-cyano-7-azabicyclo[2.2.1]heptane-7-carboxylate

Produkt 1

HCID 72444859HCID 72444859, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Triethyl amine (1.5 eq.), hydroxylamine hydrochloride (1.3 eq.) were added to a solution of benzyl 1-cyano-7-azabicyclo[2.2.1]heptane-7-carboxylate (C-37) in absolute methanol. The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, the residue was dissolved in chloroform and treated with dimethylacetylene dicarboxylate (2 eq.) for 14 hours at 60° C. The reaction mixture was then concentrated and the resulting crude oil was purified by flash chromatography (petroleum ether/EtOAc 1:1) to give the titled compound (C-38) as a mixture of isomers.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform
  3. concentrationThe reaction mixture was then concentrated
  4. customthe resulting crude oil was purified by flash chromatography (petroleum ether/EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-e6bfe532e0324573952020e64f9ed5dc
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07232819B2

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