2-Chlorobenzylamine → N-(2-chlorobenzyl)-4-hydroxy-2,2-dimethylbutanamide

HRID 655955

Reaktionsgleichung

Reaktionsgleichung von HRID 655955
[CH3:1][C:2]1([CH3:8])[CH2:6][CH2:5][O:4][C:3]1=[O:7].[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH2:12][NH2:13].C[Al](C)C.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH2:12][NH:13][C:3](=[O:7])[C:2]([CH3:8])([CH3:1])[CH2:6][CH2:5][OH:4]

Komponenten

6

Edukt 4

HCID 666482-ChlorobenzylamineHCID 947462,2-Dimethyl-4-butyrolactoneHCID 516892Sodium BicarbonateHCID 16682925Trimethylaluminum

Produkt 1

HCID 59778491N-(2-chlorobenzyl)-4-hydroxy-2,2-dimethylbutanamideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3,3-dimethyl-dihydrofuran-2(3H)-one (2.04 g, 17.9 mmol) in THF (15 mL) were added 2-chlorobenzylamine (2.4 mL, 19.9 mmol, 1.1 equiv.) and AlMe3 (2M in toluene, 4.5 mL, 9 mmol, 0.5 equiv.). The reaction mixture was stirred for 3 days. The reaction mixture was saturated NaHCO3 and extracted with EtOAc. The organic layer was washed with saturated NaHCO3, H2O and brine, dried over Na2SO4, and concentrated to give N-(2-chlorobenzyl)-4-hydroxy-2,2-dimethylbutanamide as a white solid (3.8 g, 83%), which was used without further purification. LRMS (M+H+) m/z 256.0.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with saturated NaHCO3, H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-89c2c5317b4146b2bc0841bef5b4d8a3
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071625B2

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