Methanesulfonyl chloride → 1-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-methanesulfonyloxypropyl)-2-oxopyrrolidine

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Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)([CH2:12][CH2:13][CH2:14][OH:15])[C:8]1=[O:24].[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)([CH2:12][CH2:13][CH2:14][O:15][S:33]([CH3:32])(=[O:35])=[O:34])[C:8]1=[O:24]

Komponenten

Reaktionsbedingungen

Temperatur: -5 °C

Versuchsvorschrift

Combine 1-(3,4,5-trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-hydroxypropyl)-2-oxopyrrolidine (2.6 mmol), and dichloromethane (15 mL). Cool to −5° C. using a salt-ice bath. Add dropwise, methanesulfonyl chloride (0.19 g, 1.62 mmol) at such a rate as to maintain the reaction temperature below 0° C. After 1 hour, the reaction mixture is extracted with 1 M hydrochloric acid solution and then a 5% sodium bicarbonate solution. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound: Rf=0.71 (silica gel, ethyl acetate).

Aufarbeitung

additionAdd dropwise
extractionthe reaction mixture is extracted with 1 M hydrochloric acid solution
dry with materialDry the organic layer over Na2SO4
filtrationfilter
customevaporate in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-575f9119ef2f412b8b080136e73ef3fc
Quelldatensatz: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06211199B1

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