Iodoethane → (S)-1-(benzyloxycarbonyl)-3-(N,N-diethylamino)pyrrolidine

Reaktionsgleichung

[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:23](I)[CH3:24].O1CC[CH2:28][CH2:27]1>>[CH2:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][C@H:2]([N:1]([CH2:23][CH3:24])[CH2:27][CH3:28])[CH2:3]1)=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

Edukt 4

HCID 6340Iodoethane

HCID 8028Tetrahydrofuran

HCID 11430Potassium Carbonate

HCID 1519355(S)-1-Cbz-3-Aminopyrrolidine

Produkt 1

HCID 68693001(S)-1-(benzyloxycarbonyl)-3-(N,N-diethylamino)pyrrolidine

Versuchsvorschrift

To a solution of 1.40 g of (S)-3-amino-1-(benzyloxycarbonyl)pyrrolidine (J. Med. Chem., 1992, 35, 1764-1773) in 28 ml of tetrahydrofuran, 2.6 g of potassium carbonate and 1.0 ml of ethyl iodide were added under ice-cool stirring, followed by stirring for 24 hours. The reaction solution was concentrated under reduced pressure, mixed with water, followed by extraction with ethyl acetate, and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.70 g of the objective compound as a yellow oily product.