Triethylamine → Tert-butyl [3-(4,4-dimethyl-1,3-oxazolidin-3-yl)-3-oxopropyl]carbamate

HRID 1715251

Reaktionsgleichung

Reaktionsgleichung von HRID 1715251
[CH3:1][C:2]1([CH3:7])[CH2:6][O:5][CH2:4][NH:3]1.[C:8]([NH:15][CH2:16][CH2:17][C:18](O)=[O:19])([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>C(Cl)Cl.C1CCCCC1.CCOC(C)=O>[CH3:1][C:2]1([CH3:7])[CH2:6][O:5][CH2:4][N:3]1[C:18](=[O:19])[CH2:17][CH2:16][NH:15][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 620104,4-Dimethyl oxazolidineHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 1670692-Chloro-1-methylpyridinium iodide

Produkt 1

HCID 86621990Tert-butyl [3-(4,4-dimethyl-1,3-oxazolidin-3-yl)-3-oxopropyl]carbamateAusbeute 139,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21867204Cyclohexane ethylacetateLösungsmittel

Versuchsvorschrift

To a mixture of 4,4-dimethyloxazolidine (287 μl; 2 mmol; 1 eq) and boc-beta-alanine (416.3 mg; 2.2 mmol; 1.10 eq) in DCM (30 ml), are added triethylamine (832 μl; 6 mmol; 3 eq) and 2-chloro-1-methylpyridinium iodide (1533 mg; 6 mmol; 3 eq). The mixture is stirred for 2 days at RT. The reaction is followed by TLC cyclohexane/EtOAc 1:1). The reaction mixture is then washed twice with NH4Cl sat. solution and twice with NaHCO3 sat. solution. The organic layer is dried over Na2SO4, filtered and concentrated to give 760 mg of an orange oil, which is purified by flash chromatography (cyclohexane/EtOAc gradient, from 9/1 to 1/1 over 30 min). The title product is isolated as a white-off solid (420.5 mg; 77%).

Aufarbeitung

  1. washThe reaction mixture is then washed twice with NH4Cl sat. solution and twice with NaHCO3 sat. solution
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-aebc291accbd4055ad19e939995446b1
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799814B2

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