Sodium Bicarbonate → 3-Methyl-5-[1-(4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one

HRID 515431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515431
[CH3:1][N:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16](/[N:19]=[CH:20]/[C:21]4[O:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=4)=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[O:4][C:3]1=[O:29].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CC(O)=O.CO>[CH3:1][N:2]1[N:6]=[C:5]([CH:7]2[CH2:8][CH2:9][N:10]([C:13]3[CH:14]=[CH:15][C:16]([NH:19][CH2:20][C:21]4[O:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=4)=[CH:17][CH:18]=3)[CH2:11][CH2:12]2)[O:4][C:3]1=[O:29]

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 178481743HCID 178481743, Verbindung

Produkt 1

HCID 716170383-Methyl-5-[1-(4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-oneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

3-Methyl-5-[1-(4-[(E)-1-(5-nitro-2-furyl)methylidene]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (9b, 0.40 g, 1 mmol) on reduction with sodiumcyanoborohydride (0.12 g, 2 mmol) in the presence of catalytic amount of CH3COOH (3 drops) in methanol at 0° C. for 12 h. After completion of the reaction as indicated by TLC, the reaction mixture is neutralized with sodium bi carbonate and extracted into chloroform. The crude product thus obtained was purified by column chromatography using ethyl acetate-hexane (8:2) as eluant to obtain product 3-methyl-5-[1-(4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (10b, 343 mg, 86%).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionextracted into chloroform
  3. customThe crude product thus obtained
  4. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cef4322ad6c94228bd62808f1211d5fd
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108960B2

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