Diethyl Ether → [4-(2-Methoxy-pyridin-3-yl)-4-oxo-butyl]-carbamic acid tert-butyl ester

HRID 352136

Reaktionsgleichung

Reaktionsgleichung von HRID 352136
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C(NC(C)C)(C)C.C[Li].COCN[C:22](=O)[CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].C[CH2:35][O:36]CC>O1CCCC1>[CH3:31][C:28]([O:27][C:26](=[O:32])[NH:25][CH2:24][CH2:23][CH2:22][C:35]([C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:36])([CH3:29])[CH3:30]

Komponenten

7

Edukt 5

HCID 3283Diethyl EtherHCID 7912DiisopropylamineHCID 742012-MethoxypyridineHCID 86584230[2-(Methoxymethyl-carbamoyl)-ethyl]-carbamic acid tert-butyl esterHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 102539314[4-(2-Methoxy-pyridin-3-yl)-4-oxo-butyl]-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Methoxypyridine (1.9 ml) and then diisopropylamine (0.1 ml) were added to a solution of methyl lithium (10 ml of a 1.6M solution in ether) in tetrahydrofuran (20 ml) at −78° C. and the solution was stirred at 0° C. for 18hand then re-cooled to −78° C. A solution of 1,1-dimethylethyl [3-(methoxymethylamino)-3-oxopropyl]-carbamate (1.6 g) in tetrahydrofuran (5 ml) was added slowly and the resultant solution was allowed to warm to −30° C. over 3.5 h, quenched with aqueous ammonium chloride and extracted with ether (three times). The combined organic extracts were dried (sodium sulphate), evaporated and purified by chromatography on silica eluting with petrol-ether gave the sub-title compound as a colourless oil (0.572 g).

Aufarbeitung

  1. temperaturethen re-cooled to −78° C
  2. temperatureto warm to −30° C. over 3.5 h
  3. customquenched with aqueous ammonium chloride
  4. extractionextracted with ether (three times)
  5. dry with materialThe combined organic extracts were dried (sodium sulphate)
  6. customevaporated
  7. custompurified by chromatography on silica eluting with petrol-ether

Quellen und Nachweise

ORD-Eintrag
ord-3e38315d28f442a38cbf626afe239183
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743939B2

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