Iodoethane → tert-butyl N-ethyl-N-(prop-2-yn-1-yl)carbamate

HRID 1270895

Reaktionsgleichung

Reaktionsgleichung von HRID 1270895
[H-].[Na+].[CH2:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:4]#[CH:5].[CH2:14](I)[CH3:15]>CN(C=O)C.O.C(OCC)C>[CH2:14]([N:6]([CH2:3][C:4]#[CH:5])[C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH3:15]

Komponenten

7

Edukt 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamate

Produkt 1

HCID 18366151tert-butyl N-ethyl-N-(prop-2-yn-1-yl)carbamateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A suspension of sodium hydride (354 mg, 14.2 mmol) in DMF (33 mL) at room temperature was treated with a solution of Example 516A (2.0 g, 12.9 mmol) in DMF (10 mL) and stirred for one hour at room temperature. The solution was cooled to 0° C., treated with ethyl iodide (1.24 mL, 15.5 mmol), stirred for one hour at 0° and overnight at room temperature. The solution was diluted with water (25 mL),extracted with diethyl ether (2×50 mL) and the combined organic layers were washed with brine (30 mL0, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography on silica gel using 5–10% ethyl acetate/hexanes to give the 1.1 g (47% yield) of the desired product. MS (ESI(+)) m/e 184 (M+H)+.

Aufarbeitung

  1. temperatureThe solution was cooled to 0° C.
  2. stirringstirred for one hour at 0° and overnight at room temperature
  3. washthe combined organic layers were washed with brine (30 mL0
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel using 5–10% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-32b9a24309db4d56bd758a8eab83c705
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202363B2

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