1-Ethynyl-2,2,6,6-tetramethylcyclohexanol → 2,2,2-trifluoro-N-(3-(3-((1-hydroxy-2,2,6,6-tetramethylcyclohexyl)ethynyl)phenyl)propyl)acetamide

HRID 1021099

Reaktionsgleichung

Reaktionsgleichung von HRID 1021099
[C:1]([C:3]1([OH:13])[C:8]([CH3:10])([CH3:9])[CH2:7][CH2:6][CH2:5][C:4]1([CH3:12])[CH3:11])#[CH:2].Br[C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH:18]=[CH:19][CH:20]=1>>[F:27][C:26]([F:28])([F:29])[C:25]([NH:24][CH2:23][CH2:22][CH2:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:2]#[C:1][C:3]2([OH:13])[C:4]([CH3:12])([CH3:11])[CH2:5][CH2:6][CH2:7][C:8]2([CH3:9])[CH3:10])[CH:16]=1)=[O:30]

Komponenten

3

Edukt 2

HCID 156349111-Ethynyl-2,2,6,6-tetramethylcyclohexanolHCID 57608389N-(3-(3-bromophenyl)propyl)-2,2,2-trifluoroacetamide

Produkt 1

HCID 866358552,2,2-trifluoro-N-(3-(3-((1-hydroxy-2,2,6,6-tetramethylcyclohexyl)ethynyl)phenyl)propyl)acetamide

Versuchsvorschrift

Coupling of 1-ethynyl-2,2,6,6-tetramethylcyclohexanol with bromide 10 following the method used in Example 4 gave 2,2,2-trifluoro-N-(3-(3-((1-hydroxy-2,2,6,6-tetramethylcyclohexyl)ethynyl)phenyl)propyl)acetamide as a light brown foam. Yield (0.192 g, 84%): 1H NMR (400 MHz, DMSO-d6) δ 9.40 (br s, 1H), 7.27 (t, J=7.6 Hz, 1H), 7.18-7.23 (m, 3H), 4.92 (s, 1H), 3.18 (q, J=6.8 Hz, 2H), 2.57 (t, J=7.2 Hz, 2H), 1.76 (quint, J=7.6 Hz, 2H), 1.22-1.50 (m, 6H), 1.14 (s, 6H), 1.04 (s, 6H).

Quellen und Nachweise

ORD-Eintrag
ord-aab16fb4a97340b993f7b41fe302902d
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716529B2

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