Methyl iodide → ethyl 3-(N-benzyloxycarbonyl-N-methylamino)propionate

HRID 965336

Reaktionsgleichung

Reaktionsgleichung von HRID 965336
[H-].[Na+].[CH2:3]([O:10][C:11]([NH:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:21]I>O1CCCC1.CN(C)C=O.O.CCCCCC.C(OCC)(=O)C>[CH2:3]([O:10][C:11]([N:13]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:21])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

9

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12116647Ethyl 3-{[(benzyloxy)carbonyl]amino}propanoate

Produkt 1

HCID 22629164ethyl 3-(N-benzyloxycarbonyl-N-methylamino)propionate

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (1.92 g, 60% in Oil) in a mixture of tetrahydrofuran (200 ml) and N,N-dimethylformamide (50 ml) was added dropwise ethyl 3-(benzyloxycarbonylamino)propionate (10 g) at 30° C. under nitrogen atmosphere, which was stirred for 30 minutes. To the reaction mixture was added methyl iodide (3 ml) and stirred for additional 6 hours. To the resulting mixture was added carefully water (5 ml), which was poured into a mixture of ethyl acetate (500 ml), n-hexane (150 ml) and water (100 ml). Organic layer was separated, washed in turn with water (100 ml×3), 1N-aqueous hydrochloric acid (100 ml), brine (100 ml), saturated sodium hydrogen carbonate in water (100 ml) and brine (100 ml×2), and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (250 ml) eluting in turn with n-hexane, 10%, 50% ethyl acetate in n-hexane to give ethyl 3-(N-benzyloxycarbonyl-N-methylamino)propionate (8.32 g).

Aufarbeitung

  1. stirringstirred for additional 6 hours
  2. customOrganic layer was separated
  3. washwashed in turn with water (100 ml×3), 1N-aqueous hydrochloric acid (100 ml), brine (100 ml), saturated sodium hydrogen carbonate in water (100 ml) and brine (100 ml×2)
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgave a residue, which
  7. customwas chromatographed on silica gel (250 ml)
  8. washeluting in turn with n-hexane, 10%, 50% ethyl acetate in n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-d7dbe4052c724a358ab8a88e32795912
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05773530

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