Tetrahydrofuran → HCID 178440768, Verbindung

HRID 2242255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2242255
[CH2:1]([N:3](CC)CC)C.[CH2:8]1[CH2:12]OC[CH2:9]1.[CH2:13]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:27][N:26]=[C:25]([C:28]3[CH:35]=[CH:34][C:31](C=O)=[CH:30][CH:29]=3)[N:24]=2)=[CH:19][CH:18]=1)[CH:14]([CH3:16])[CH3:15].C(O[BH-]([O:45][C:46](=[O:48])[CH3:47])OC(=O)C)(=O)C.[Na+].[C:50](O)(=O)C.[CH2:54]1[CH2:58]OC[CH2:55]1>CO>[C:54]([O:45][C:46]([C@H:47]1[CH2:12][C@@H:8]([NH:3][CH2:1][C:31]2[CH:34]=[CH:35][C:28]([C:25]3[N:24]=[C:23]([C:20]4[CH:19]=[CH:18][C:17]([CH2:13][CH:14]([CH3:15])[CH3:16])=[CH:22][CH:21]=4)[O:27][N:26]=3)=[CH:29][CH:30]=2)[CH2:9]1)=[O:48])([CH3:55])([CH3:58])[CH3:50]

Komponenten

7

Edukt 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 184469664-[5-[4-(2-Methylpropyl)phenyl]-1,2,4-oxadiazol-3-YL]benzaldehydeHCID 23444217Acetic acid tetrahydrofuran

Produkt 1

HCID 178440768HCID 178440768, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 3-cis-amino-cylcobutanecarboxylic acid tert-butyl ester (3.78 g, 19.6 mmol), triethylamine (4.0 mL, 29.4 mmol) and THF (100 mL) was added to a solution of 4-[5-(4-isobutyl-phenyl)-[1,2,4]oxadiazol-3-yl]-benzaldehyde (6.0 g, 19.6 mmol) in acetic acid/THF (1:10, 100 mL) and stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (8.06 g, 39.2 mmol) was added to the reaction mixture, stirred at room temperature for 12 hours, treated with methanol (50.0 mL) and concentrated in vacuo. The resulting residue was taken up in dichloromethane, washed sequentially with brine, saturated NaHCO3 and brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash chromatography (silica, 1:9-1:1 EtOAc:hexanes) provided the title compound (4.0 g, 44% yield) as a solid.

Aufarbeitung

  1. stirringstirred at room temperature for 12 hours
  2. concentrationconcentrated in vacuo
  3. washwashed sequentially with brine, saturated NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (silica, 1:9-1:1 EtOAc:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6d136bed5041475caa5d756bb0b224bd
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07671043B2

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