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

HRID 338079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338079
[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].[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[Li]>O1CCCC1>[CH2:1]([N:4]([CH2:12][C:13](=[O:14])[C:20]1[S:19][CH:23]=[CH:22][CH:21]=1)[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 178418439HCID 178418439, Verbindung

Produkt 1

HCID 86697895tert-Butyl N-allyl-N-[2-oxo-2-(2-thienyl)ethyl]carbamateAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl N-allyl-N-[2-(methoxy(methyl)amino)-2-oxo-ethyl]carbamate (25 g, 96.8 mmol) in tetrahydrofuran (339 mL) at −78° C. is added drop wise 2-thienyllithium (145 ml, 1 M in tetrahydrofuran) over 20 min. The reaction is carefully quenched with aqueous ammonium chloride (20 mL), diluted with water (100 mL), and extracted with dichloromethane. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated 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 (15.2 g, 56%). ES/MS (m/e): 182 (M+H-100).

Aufarbeitung

  1. customThe reaction is carefully quenched with aqueous ammonium chloride (20 mL)
  2. additiondiluted with water (100 mL)
  3. extractionextracted with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  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-f68aa4a492dd4f91b1e8023167a98ad7
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889856B2

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