4-Acetyl-piperidine-1-carboxylic acid tert-butyl ester → tert-Butyl 4-(1-hydroxy-1-methyl-3-phenylprop-2-ynyl)piperidine-1-carboxylate

HRID 1896004Notizen

Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:16])[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]1([C:23]#[C:24][Mg]Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[OH:16][C:14]([CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:13][CH2:12]1)([CH3:15])[C:24]#[C:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

Into a solution of 4-acetylpiperidine-1-carboxylic acid tert-butyl ester (0.67 g, 2.95 mmol), prepared as described in WO2004041777, in THF (20 mL) cooled at −10° C. was dropped a 1M solution of phenylethynylmagnesium bromide in THF (4.5 mL, 4.5 mmol). The reaction mixture was stirred at room temperature overnight. Afterwards, it was quenched with a saturated aq. solution of ammonium chloride and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with Petroleum Ether-EtOAc 7:3, affording the title product as a pale yellow oil.

Aufarbeitung

customAfterwards, it was quenched with a saturated aq. solution of ammonium chloride
extractionextracted with EtOAc
washThe combined organic layers were washed with brine
customdried on Na2SO4
customevaporated to dryness in vacuo
customto afford a residue, which
customwas purified by automated flash liquid chromatography (Horizon™-Biotage)
washeluting with Petroleum Ether-EtOAc 7:3

Quellen und Nachweise

ORD-Eintrag: ord-105e6dd215ca4b81bee594ccbd9d85a7
Quelldatensatz: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08518916B2

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