1,2-Dichloroethane → tert-Butyl 3-carbamoylmorpholine-4-carboxylate

HRID 385988

Reaktionsgleichung

Reaktionsgleichung von HRID 385988
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])[CH3:3].[Cl-].[NH4+].C(Cl)CCl.C1C=CC2N(O)N=[N:29]C=2C=1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:29][C:14]([CH:9]1[CH2:10][O:11][CH2:12][CH2:13][N:8]1[C:6]([O:5][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:7])=[O:16]

Komponenten

8

Edukt 6

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27601334-(tert-Butoxycarbonyl)morpholine-3-carboxylic acid

Produkt 1

HCID 21098189tert-Butyl 3-carbamoylmorpholine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-{[(1,1-Dimethylethyl)oxy]carbonyl}morpholine-3-carboxylic acid (0.5 g, 2.162 mmol), ammonium chloride (0.347 g, 6.49 mmol), EDC (0.622 g, 3.24 mmol), HOBt (0.993 g, 6.49 mmol) and DIPEA (1.699 mL, 9.73 mmol) were stirred in DMF (10 mL) at room temperature overnight. Saturated NaHCO3 was then added and the mixture was extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as a yellow gum.

Aufarbeitung

  1. extractionthe mixture was extracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-12587f8de4164529bd243ea643c98784
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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