Potassium Carbonate → 1-(1-Naphthalen-1-yl-ethyl)-aziridine-2-carboxylic acid methyl ester

HRID 222486

Reaktionsgleichung

Reaktionsgleichung von HRID 222486
[C:1]1([C@@H:11]([NH2:13])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:21]([CH2:26]Br)[C:22]([O:24][CH3:25])=[O:23]>C(#N)C>[CH3:25][O:24][C:22]([CH:21]1[CH2:26][N:13]1[CH:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH3:12])=[O:23]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 663251-Naphthalenemethanamine, alpha-methyl-, (alphaS)-HCID 95428Methyl 2,3-dibromopropionate

Produkt 1

HCID 866010811-(1-Naphthalen-1-yl-ethyl)-aziridine-2-carboxylic acid methyl esterAusbeute 78,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of (S)-(−)-1-(1-naphthyl)ethylamine (20.8 g, 120 mmol) in acetonitrile (HPLC grade, 600 mL) is added K2CO3 (52.7 g, 360 mmol) and methyl 2,3-dibromopropionate (30 g, 120 mmol). The solution is stirred overnight at room temperature. The solution is evaporated to dryness, then H2O/EtOAc (1:1) (600 mL) is added, and the mixture is extracted with EtOAc (4×100 mL). The organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:2) to provide 24 g (78%) of the title compound as a mixture of two diastereomers in an equimolecular ratio. M+H+=256.10.

Aufarbeitung

  1. customThe solution is evaporated to dryness
  2. additionH2O/EtOAc (1:1) (600 mL) is added
  3. extractionthe mixture is extracted with EtOAc (4×100 mL)
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customThe residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-94f6744d9a3e470ebbf30da455dc7c3b
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207183B2

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