Potassium Iodide → 1-(4,4-Diphenyl-3-butenyl)-cis-4-hydroxy-3-piperidinecarboxylic acid methyl ester

HRID 851303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851303
Cl.[CH3:2][O:3][C:4]([C@H:6]1[C@@H:11]([OH:12])[CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5].[C:13]1([C:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH2:21][CH2:22]Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[CH3:2][O:3][C:4]([C@H:6]1[C@@H:11]([OH:12])[CH2:10][CH2:9][N:8]([CH2:22][CH2:21][CH:20]=[C:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:7]1)=[O:5]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 104017744,4-Diphenyl-3-butenyl bromideHCID 131712984Methyl cis-4-hydroxy-3-piperidinecarboxylate hydrochloride

Produkt 1

HCID 705351181-(4,4-Diphenyl-3-butenyl)-cis-4-hydroxy-3-piperidinecarboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Similarly, a mixture of 1.63 g. (0.00835 mole) of cis-4-hydroxy-3-piperidinecarboxylic acid methyl ester, hydrochloride, 3 g. (0.0104 mole) of 4,4-diphenyl-3-butenyl bromide, 1.5 g. of potassium carbonate and 0.2 g. of potassium iodide in 50 ml. of dimethylformamide was reacted as described above to give 1-(4,4-diphenyl-3-butenyl)-cis-4-hydroxy-3-piperidinecarboxylic acid methyl ester. This ester (1.4 g., 0.0038 mole) was hydrolyzed in 50 ml. of hot 6 N hydrochloric acid to obtain 1-(4,4-diphenyl-3-butenyl)-cis-4-hydroxy-3-piperidinecarboxylic acid hydrochloride, m.p. 174°-177° C.

Aufarbeitung

  1. additionSimilarly, a mixture of 1.63 g

Quellen und Nachweise

ORD-Eintrag
ord-52acbb0744224be798f669bd915dd23f
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04383999

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