Aluminium lithium hydride → 1-benzyl-N,4-dimethylpiperidin-3-amine

HRID 7211

Reaktionsgleichung

CO[C:3](=O)[NH:4][C@H:5]1[C@@H:10]([CH3:11])[CH2:9][CH2:8][N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:12]([N:7]1[CH2:8][CH2:9][CH:10]([CH3:11])[CH:5]([NH:4][CH3:3])[CH2:6]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

The reduction of cis-(1-benzyl-4-methyl-piperidin-3-yl)-carbamic acid methyl ester was performed by charging 2 grams substrate (1 equiv., 7.62 mmol) to a solution of 20 ml THF (10 volumes) and 15.2 ml 1 M LAH in THF (2 equiv., 15.2 mmol). The addition was performed at a rate so that the temperature reached 30°-40° C. and then the reaction was allowed to cool to 20° C. The reaction was worked up by quenching with 40 ml Rochelle Salt (20 volumes) to a temperature of 35° C. and then extracting the product 2 times into 20 ml methylene chloride (10 volumes). The filtrate was then concentrated to a clear and colorless oil. (90% yield). Note that the starting material needs to be clean in order for this reaction to proceed in high yield.

Aufarbeitung

additionThe addition
customreached 30°-40° C.
customby quenching with 40 ml Rochelle Salt (20 volumes) to a temperature of 35° C.
extractionextracting the product 2 times into 20 ml methylene chloride (10 volumes)
concentrationThe filtrate was then concentrated to a clear and colorless oil
customto be clean in order for this reaction

Quellen und Nachweise

ORD-Eintrag: ord-d62a9641240d4a0b86f430ec8ac9107d
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07084277B2

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