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

HRID 1744867Notes

Reaction equation

HRID 1744867 reaction equation
[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

Participants

3

Reactant 2

HCID 219101TraxoprodilHCID 38061142,3-Dihydroxybutanedioate

Product 1

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

Procedure

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.

Sources & evidence

ORD record
ord-39f4558186d9422bbc5a54bb9211e51a
Source dataset
uspto-grants-2006_03
Patent number
US07019016B2

Reaction notes

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