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

HRID 1744867

Reaktionsgleichung

Reaktionsgleichung von HRID 1744867
[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. Pat. No. 6,008,233 (issued Dec. 28, 1999), referred to above, and as exemplified in Example 1 below.

Quellen und Nachweise

ORD-Eintrag
ord-39f4558186d9422bbc5a54bb9211e51a
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07019016B2

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