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

HRID 1423296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1423296
[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 CHH23NO, 186.20; found, 186.0).

Quellen und Nachweise

ORD-Eintrag
ord-0c20c019c60942a0947b63d870d19fc7
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927573B2

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