Dimethylacetamide → HCID 178457241, Verbindung

Reaktionsgleichung

[C:1]([O:5][C:6](=[O:21])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19]Br)[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:22]([CH2:25][NH2:26])[CH:23]=C.[CH3:27]C(N(C)C)=O>>[C:1]([O:5][C:6](=[O:21])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][N:26]([CH2:25][CH:22]=[CH2:23])[CH3:27])[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Komponenten

Edukt 3

HCID 31374Dimethylacetamide

HCID 4437323-Buten-1-amine

HCID 178486057HCID 178486057, Verbindung

Produkt 1

HCID 178457241HCID 178457241, VerbindungAusbeute 92 %

Versuchsvorschrift

To 1.7 g (4.7 mmol) trans-[4-(4-Bromo-butoxy)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 22 ml DMA, 1.34 ml (14 mmol, 3 eq) N-allylmethylamine were added over a period of 10 min. The reaction was stirred at RT over night, concentrated and the residue was dissolved in CH2Cl2/5% aqueous NaHCO3. The phases were separated and the inorganic phase was extracted with CH2Cl2, the combined organic phases were washed with brine, dried over Na2SO4 and concentrated to yield 1.5 g (92%) trans-(4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl)-methyl-carbamic acid tert-butyl ester as colorless oil, MS: 355 (MH+).