Cesium carbonate → 1-(4-(1-Acetyl-4-[4-(2,3-dihydroxypropoxy)-3-methylphenyl]-piperidin-4-yl}-2-methylphenoxy)-3,3-dimethylbutan-2-one

HRID 250183

Reaction equation

HRID 250183 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]([C:18]2[CH:31]=[CH:30][C:21]([O:22][CH2:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[C:20]([CH3:32])[CH:19]=2)([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([CH3:17])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].ClCC(=O)C(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:47]1[O:49][C@H:48]1[CH2:50][OH:51]>>[C:1]([N:4]1[CH2:9][CH2:8][C:7]([C:18]2[CH:31]=[CH:30][C:21]([O:22][CH2:23][C:24](=[O:29])[C:25]([CH3:26])([CH3:27])[CH3:28])=[C:20]([CH3:32])[CH:19]=2)([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:47][CH:48]([OH:49])[CH2:50][OH:51])=[C:12]([CH3:17])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 835721-ChloropinacoloneHCID 6973630(-)-GlycidolHCID 668895931-{4-[1-Acetyl-4-(4-hydroxy-3-methylphenyl)-piperidin-4-yl]-2-methylphenoxy)-3,3-dimethylbutan-2-one2×

Product 1

HCID 668910911-(4-(1-Acetyl-4-[4-(2,3-dihydroxypropoxy)-3-methylphenyl]-piperidin-4-yl}-2-methylphenoxy)-3,3-dimethylbutan-2-one

Procedure

In a manner similar to that described for Example 6B, 1-{4-[1-acetyl-4-(4-hydroxy-3-methylphenyl)-piperidin-4-yl]-2-methylphenoxy)-3,3-dimethylbutan-2-one was prepared by using 1 equiv of 1-chloropinacolone and cesium carbonate. 1-{4-[1-Acetyl-4-(4-hydroxy-3-methylphenyl)-piperidin-4-yl]-2-methylphenoxy}-3,3-dimethylbutan-2-one was then alkylated with (S)-glycidol as in Example 1H to yield 1-(4-(1-acetyl-4-[4-(2,3-dihydroxypropoxy)-3-methylphenyl]-piperidin-4-yl}-2-methylphenoxy)-3,3-dimethylbutan-2-one.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-5254087fae8e4c8fbde357d42b4b127c
Source dataset
uspto-grants-2011_01
Patent number
US07863298B2

Linked notes

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