Ethyl bromoacetate → Ethyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-1-piperidineacetate

HRID 634615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 634615
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][NH:11][C:10]1=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:10]1=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 21260262tert-Butyl (2-oxopiperidin-3-yl)carbamate

Produkt 1

HCID 21260261Ethyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-1-piperidineacetateAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(3RS)-3-tert-butoxycarbonylaminopiperidin-2-one (16.07 g) was dissolved in N,N-dimethylformamide (DMF, 350 ml) and the mixture was cooled to 0° C. Sodium hydride (3.6 g of a 50% dispersion in mineral oil) was added and then the mixture was stirred at 0° C. for one hour. A solution of ethyl bromoacetate (13.78 g) in DMF (20 ml) was then added. The mixture was stirred for 16 hours at ambient temperature, then cooled to 0° C. and ice added. Volatile material was removed by evaporation and the residue was partitioned between ethyl acetate and brine. The organic layer was washed with brine, dried over Na2SO4 and concentrated by evaporation. The resulting oil was purified on silica eluting with 40% ethyl acetate/petroleum ether (60-80° C.) to give ethyl 2-[(3RS)-3-tert-butoxycarbonylamino-2-oxopiperidin-1-yl]acetate as a colourless oil (18.15 g).

Aufarbeitung

  1. stirringThe mixture was stirred for 16 hours at ambient temperature
  2. temperaturecooled to 0° C.
  3. additionice added
  4. customVolatile material was removed by evaporation
  5. customthe residue was partitioned between ethyl acetate and brine
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated by evaporation
  9. customThe resulting oil was purified on silica eluting with 40% ethyl acetate/petroleum ether (60-80° C.)

Quellen und Nachweise

ORD-Eintrag
ord-553aba9a25e1417bae03224d9fd5b172
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06184207B2

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