Ethyl bromoacetate → Methyl {2-[(benzyloxy)methyl]aziridin-1-yl}acetate

HRID 2109845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2109845
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:12][NH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.Br[CH2:23][C:24]([O:26][CH2:27]C)=[O:25]>ClCCl>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:12][N:11]1[CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 866027862-[(Benzyloxy)methyl]aziridine

Produkt 1

HCID 57634653Methyl {2-[(benzyloxy)methyl]aziridin-1-yl}acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a cold (−78° C.) solution of 2-[(benzyloxy)methyl]aziridine (0.42 g, 2.57 mmol) and N,N-diisopropylethylamine (0.5 mL, 2.90 mmol) in dichloromethane (15 mL) under an atmosphere of nitrogen, ethyl bromoacetate (0.39, 2.5 mmol) was added over a period of 1 h. The resultant mixture was allowed to slowly warm up to room temperature and stirred overnight. The resultant mixture was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a mixture of 70% ethyl acetate in hexane. Collection and concentration of appropriate fractions provided the title compound.

Aufarbeitung

  1. washThe resultant mixture was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. additionThe residue was subjected to column chromatography on silica gel eluting with a mixture of 70% ethyl acetate in hexane
  6. customCollection and concentration of appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-05619cf4335748e0b8826f7da7a75642
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517532B2

Notizen zur Reaktion

Wird geladen…