Traxoprodil → 1-[(1s,2s)-2-Hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]-4-phenylpiperidin-4-ol

HRID 861909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 861909
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([OH:24])[C@@H:9]([N:11]2[CH2:16][CH2:15][C:14]([OH:23])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)[CH3:10])=[CH:4][CH:3]=1.C(C(C(C([O-])=O)O)O)([O-])=O>>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:24])[CH:9]([N:11]2[CH2:12][CH2:13][C:14]([OH:23])([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:15][CH2:16]2)[CH3:10])=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 219101TraxoprodilHCID 38061142,3-Dihydroxybutanedioate

Produkt 1

HCID 100650201-[(1s,2s)-2-Hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]-4-phenylpiperidin-4-ol

Versuchsvorschrift

A preferred compound, (1S,2S)-1-(4-hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-1-propanol ((1S,2S) free base), and its tartrate salt, can be prepared as described in U.S. Pat. No. 5,272,160, referred to above. The resolution of racemic 1-(4-hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-1-propanol to form the (1S,2S) free base and the corresponding (1R,2R) enantiomer can be carried out as described in U.S. provisional patent application entitled "(1S,2S)-1-(4-Hydroxyphenyl)-2-(4-Hydroxy-4-Phenylpiperidin-3-yl)-1-Propanol Methanesulfonate Trihydrate", referred to above, and as exemplified in Example 1 below.

Quellen und Nachweise

ORD-Eintrag
ord-0e6c61dc5a824d1ea170aa20aa77b17e
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716961

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