Triethylamine → Benzyl (1,4-dioxan-2-ylmethyl)methylcarbamate

HRID 1987098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1987098
Cl.[O:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[CH2:8][NH:9][CH3:10].[CH:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][C:19](Cl)=[O:20])=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[O:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[CH2:8][N:9]([CH3:10])[C:19](=[O:20])[O:18][CH2:17][C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 66972118(1,4-Dioxan-2-ylmethyl)methylamine hydrochloride

Produkt 1

HCID 66972115Benzyl (1,4-dioxan-2-ylmethyl)methylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-(1,4-dioxan-2-yl)-N-methylmethanamine hydrochloride (4.83 g, 29 mmol) was dissolved in 100 mL dichloromethane. Benzyl chloridocarbonate (4.9 mL, 35 mmol) and triethylamine (10 mL, 72 mmol) were added. The solution was stirred at ambient temperature. After 12 hours, the solution was concentrated, then diluted with ethyl acetate, and washed with saturated sodium bicarbonate and water. The organic layer was separated, dried with magnesium sulfate, filtered, concentrated in vacuo, and purified by silica chromatography (0-100% ethyl acetate/hexanes gradient) to afford the title compound (racemic mixture).

Aufarbeitung

  1. concentrationthe solution was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate and water
  4. customThe organic layer was separated
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by silica chromatography (0-100% ethyl acetate/hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-a17ec260842f4882b1e0dc5adf8f1eb8
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550478B2

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