Triethylamine → N-(3-Benzyloxy-2-hydroxy-propyl)-N-ethyl-methanesulfonamide

HRID 1027574

Reaktionsgleichung

C(N(CC)CC)C.[CH2:8]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH3:9].[CH2:15]([O:22][CH2:23][CH:24]1[CH2:26][O:25]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCOCC1>[CH2:15]([O:22][CH2:23][CH:24]([OH:25])[CH2:26][N:10]([CH2:8][CH3:9])[S:11]([CH3:14])(=[O:13])=[O:12])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

Triethylamine (0.043 ml, 0.1 equiv) was added to a mixture of N-ethylmethanesulfonamide (413 mg, 1.1 equiv) and 2-benzyloxymethyloxirane (500 mg, 3.04 mmol) prepared according to (J. Am. Chem. Soc., 1996, 118, 7094-7100) in anhydrous dioxane (1 ml). The reaction mixture was then heated to 50° C. overnight. As the reaction was not complete, it was heated to 100° C. for another 5 hours (reaction complete according to TLC). The volatiles were then removed in vacuo. Flash chromatography eluting with cyclohexane/Ethyl acetate (6/4 then 1/1) afforded 836 mg (2.91 mmol, 96%). LCMS (Method E) 1.44 min, M+H 288. 1H-NMR (CDCl3, 400 MHz): 7.43-7.27 (m, 5H), 4.57 (s, 2H), 4.11-3.90 (m, 1H), 3.62-3.44 (m, 2H), 3.43-3.20 (m, 4H), 2.90 (s, 3H), 1.14-1.33 (m, 3H).

Aufarbeitung

customprepared
temperatureit was heated to 100° C. for another 5 hours
custom(reaction complete according to TLC)
customThe volatiles were then removed in vacuo
washFlash chromatography eluting with cyclohexane/Ethyl acetate (6/4
custom1/1) afforded 836 mg (2.91 mmol, 96%)
customLCMS (Method E) 1.44 min, M+H 288

Quellen und Nachweise

ORD-Eintrag: ord-3dcbbfab650a440a8f65dfc99e4fe798
Quelldatensatz: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08735362B2

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