Triethylamine → (4R)-4-Methyl-4-[2-(1-methyl-1H-pyrrol-2-yl)ethyl]-1,3-oxazolidin-2-one

HRID 604550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604550
[NH2:1][C@:2]([CH3:13])([CH2:5][CH2:6][C:7]1[N:8]([CH3:12])[CH:9]=[CH:10][CH:11]=1)[CH2:3][OH:4].[C:14](OC(OC(C)(C)C)=O)(OC(C)(C)C)=[O:15].C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:13][C@@:2]1([CH2:5][CH2:6][C:7]2[N:8]([CH3:12])[CH:9]=[CH:10][CH:11]=2)[CH2:3][O:4][C:14](=[O:15])[NH:1]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 66672978HCID 66672978, Verbindung

Produkt 1

HCID 18448138(4R)-4-Methyl-4-[2-(1-methyl-1H-pyrrol-2-yl)ethyl]-1,3-oxazolidin-2-oneAusbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The obtained (2R)-2-amino-2-methyl-4-(1-methylpyrrol-2-yl)butan-1-ol 1/2 D-(−)-tartrate (41.4 mg, 0.16 mmol) was suspended in methylene chloride (1.6 mL) and di-t-butyl dicarbonate (0.176 g, 0.810 mmol), triethylamine (0.225 mL, 1.62 mmol) and 4-dimethylaminopyridine (2.0 mg, 0.016 mmol) were added thereto, followed by stirring of the mixture at room temperature for 30 minutes. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate 3:2-2:1) to obtain (4R)-4-methyl-4-[2-(1-methylpyrrol-2-yl)ethyl]-1,3-oxazolidin-2-one (17.7 mg, yield: 53%).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate 3:2-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-cbabe87644a34bde879b34c0057bbe41
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910617B2

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