2-Methyltetrahydrofuran → tert-Butyl 1-(3-methyl-1,2,4-oxadiazole-yl)-3-azabicyclo[3.1.0]hexan-3-carboxylate

HRID 705692

Reaktionsgleichung

Reaktionsgleichung von HRID 705692
CC1CCCO1.[C:7](=[N:10][OH:11])([NH2:9])[CH3:8].C[O-].[Na+].[C:15]12([C:28](OCC)=O)[CH2:20][CH:19]1[CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]2>O>[CH3:8][C:7]1[N:9]=[C:28]([C:15]23[CH2:20][CH:19]2[CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]3)[O:11][N:10]=1

Komponenten

6

Edukt 4

HCID 73012-MethyltetrahydrofuranHCID 30926N-HydroxyacetamidineHCID 10942334Sodium MethoxideHCID 53249947Ethyl 3-Boc-3-azabicyclo[3.1.0]hexane-1-carboxylate

Produkt 1

HCID 58487578tert-Butyl 1-(3-methyl-1,2,4-oxadiazole-yl)-3-azabicyclo[3.1.0]hexan-3-carboxylateAusbeute 53,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2-Methyltetrahydrofuran (15 mL), acetamide oxime (2.54 g, 34.3 mmol) and sodium methoxide (3.70 g, 68.6 mmol) were added to 3-tert-butyl 1-ethyl 3-azabicyclo[3.1.0]hexane-1,3-dicarboxylate (103) (3.5 g, 13.72 mmol) and the mixture was heated to reflux for 20 minutes. Upon cooling the suspension was treated with 60 mL, of water and extracted with ethyl acetate (2×50 mL). The combined organics were washed with saturated sodium chloride and dried over magnesium sulfate. The mixture was concentrated and the residue was chromatographed over 20 g of silica gel with hexanes/ethyl acetate; obtained 1.95 g of 104 as a white solid. MS (ESI) m/z 304.0[M+K]+. 1H NMR (CDCl3) δ: 1.17 (m, 1H), 1.46 (s, 9H), 1.74 (m, 1H), 2.18 (s, 2H), 2.22 (m, 1H), 2.36 (s, 3H), 3.50 (m, 1H), 3.70 (m, 1H).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 20 minutes
  3. temperatureUpon cooling the suspension
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. washThe combined organics were washed with saturated sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe mixture was concentrated
  8. customthe residue was chromatographed over 20 g of silica gel with hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4264118aa6634663abba845a18446ad0
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174972B2

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