Lithium diisopropylamide → 4-[2-{1-(Triphenylmethyl)-4-imidazolyl}ethenyl]-1-phenylpiperidine

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Reaktionsgleichung

C(OP([CH2:9][C:10]1[N:11]=[CH:12][N:13]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=1)(OCC)=O)C.[Li+].CC([N-]C(C)C)C.[CH:42]([CH:44]1[CH2:49][CH2:48][N:47]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:46][CH2:45]1)=O>C1COCC1>[C:28]1([C:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:13]2[CH:14]=[C:10]([CH:9]=[CH:42][CH:44]3[CH2:49][CH2:48][N:47]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[CH2:46][CH2:45]3)[N:11]=[CH:12]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

The product from Step D is dissolved in THF and cooled to −78° C. under nitrogen. A solution of LDA in THF is added dropwise. The reaction was stirred at −78° C. for 1 h, then a solution of 4-formyl-1-phenylpiperidine from Step A is added, and the reaction warmed to room temperature overnight. The reaction is quenched with ammonium chloride solution, and extracted with ethyl acetate. The title compound is obtained after chromatography on silica gel.

Aufarbeitung

temperaturethe reaction warmed to room temperature overnight
customThe reaction is quenched with ammonium chloride solution
extractionextracted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-a7c670ef23594b0cb0b70aa2534de37c
Quelldatensatz: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06248756B1

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