tert-Butyl N-allyl-N-[2-(methoxy(methyl)amino)-2-oxo-ethyl]carbamate → tert-Butyl N-allyl-N-phenacyl-carbamate

HRID 470205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 470205
[CH2:1]([N:4]([CH2:12][C:13](N(OC)C)=[O:14])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3].[C:19]1([Mg]Br)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[CH2:1]([N:4]([CH2:12][C:13]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:14])[C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH:2]=[CH2:3]

Komponenten

4

Edukt 2

HCID 86697892tert-Butyl N-allyl-N-[2-(methoxy(methyl)amino)-2-oxo-ethyl]carbamateHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 86697893tert-Butyl N-allyl-N-phenacyl-carbamateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl N-allyl-N-[2-(methoxy(methyl)amino)-2-oxo-ethyl]carbamate (4.0 g, 15.5 mmol) in THF (54 mL) cooled to −20° C. is added drop wise phenyl magnesium bromide (10.3 ml, 3 M in diethyl ether). The reaction is monitored by TLC, carefully quenched with saturated ammonium chloride in water (20 mL), diluted with water (100 mL) and extracted with dichloromethane. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by silica gel flash chromatography, eluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (5:1) to give the title compound (3.2 g, 75%). 1H NMR (CDCl3) Mixture of two rotamers (51:49) δ 1.47, 1.35 (s, 9H), 3.91, 3.99 (d, 2H), 4.52, 4.65 (s, 2H), 5.07-5.16 (m, 2H), 5.72-5.87 (m, 1H), 7.41-7.50 (m, 2H), 7.52-7.60 (m, 1H), 7.88-7.95 (m, 2H).

Aufarbeitung

  1. customcarefully quenched with saturated ammonium chloride in water (20 mL)
  2. additiondiluted with water (100 mL)
  3. extractionextracted with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue
  8. customThe residue is purified by silica gel flash chromatography
  9. washeluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-1193acf4d71f42888e9e1eb02fa324b3
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629270B2

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