Ethyl 4-oxobutanoate → 4-[N-Dodecyl-N-[2-[4-(3,3-Dimethoxy-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]amino]butanoic acid, ethyl ester

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Reaktionsgleichung

[CH3:1][O:2][C:3]([O:32][CH3:33])([C:28]([F:31])([F:30])[F:29])[CH2:4][CH2:5][C:6]1[CH:27]=[CH:26][C:9]([O:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:8][CH:7]=1.C([BH3-])#N.[Na+].O=[CH:39][CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43]>CO.C(OCC)C>[CH2:14]([N:13]([CH2:39][CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:12][CH2:11][O:10][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][C:3]([O:2][CH3:1])([O:32][CH3:33])[C:28]([F:30])([F:31])[F:29])=[CH:27][CH:26]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Komponenten

Reaktionsbedingungen

Temperatur: 22 °C

Versuchsvorschrift

A solution of N-[2-[4-(3,3-dimethoxy-4,4,4-trifluorobut-1-yl)phenoxy]-ethyl]dodecanamine (2.0 g, 4.2 mmol) in methanol (50 ml) was treated with sodium cyanoborohydride (0.55 g, 8.4 mmol) and ethyl 4-oxobutyrate (1.04 g, 8.4 mmol). The resulting mixture was stirred at 22° C. for 16 h, diluted with diethyl ether (350 ml), washed with water (200 ml), brine (200 ml), dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (hexane/AcOEt 9:1 to 6:1) to afford the title compound (1.8 g, 73%) as a liquid.

Aufarbeitung

washwashed with water (200 ml), brine (200 ml)
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel (hexane/AcOEt 9:1 to 6:1)

Quellen und Nachweise

ORD-Eintrag: ord-c3cd23191cc448b5a702e36209016de8
Quelldatensatz: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06255496B1

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