Ethanolamine → 2-((3-Cyclohexylpropyl)amino)ethanol

HRID 2383284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383284
[CH2:1]([CH2:3][NH2:4])[OH:2].[CH:5]1([CH2:11][CH2:12][CH:13]=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:5]1([CH2:11][CH2:12][CH2:13][NH:4][CH2:3][CH2:1][OH:2])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Komponenten

5

Edukt 3

HCID 700EthanolamineHCID 78070CyclohexanepropionaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 5417632-((3-Cyclohexylpropyl)amino)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of ethanolamine (0.44 g, 7.1 mmol) in DCM (15 mL) at 0° C. was added a solution of 3-cyclohexylpropionaldehyde (1.0 g, 7.1 mmol) in DCM (10 mL) followed by sodium triacetoxyborohydride (1.67 g, 7.86 mmol). The resulting mixture was warmed to room temperature. After 2.5 hours the desired product was observed by mass spectrometric analysis. The reaction mixture was stirred overnight, then diluted with DCM (50 mL), washed with saturated sodium bicarbonate (2×50 mL), and brine (50 mL), dried over sodium sulfate, filtered, and concentrated to give a clear oil (1.0 g) which was used in the next step without further purification. ((m/z): [M+H]+ calcd for C11H23NO, 186.20. found, 186.0).

Quellen und Nachweise

ORD-Eintrag
ord-ff9e7b98d05a4c3fa4e56277c1e28d80
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263618B2

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