Reaction #337365

ord-5254087fae8e4c8fbde357d42b4b127c

Reaction equation

CC(=O)N1CCC(c2ccc(O)c(C)c2)(c2ccc(OCC(=O)C(C)(C)C)c(C)c2)CC1
1-{4-[1-Acetyl-4-(4-hydroxy-3-methylphenyl)-piperidin-4-yl]-2-methylphenoxy}-3,3-dimethylbutan-2-one
CC(=O)N1CCC(c2ccc(O)c(C)c2)(c2ccc(OCC(=O)C(C)(C)C)c(C)c2)CC1
1-{4-[1-acetyl-4-(4-hydroxy-3-methylphenyl)-piperidin-4-yl]-2-methylphenoxy)-3,3-dimethylbutan-2-one
CC(C)(C)C(=O)CCl
1-chloropinacolone
OC[C@H]1CO1
(S)-glycidol
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
→
CC(=O)N1CCC(c2ccc(OCC(=O)C(C)(C)C)c(C)c2)(c2ccc(OCC(O)CO)c(C)c2)CC1
1-(4-(1-acetyl-4-[4-(2,3-dihydroxypropoxy)-3-methylphenyl]-piperidin-4-yl}-2-methylphenoxy)-3,3-dimethylbutan-2-one

Reactants

CC(=O)N1CCC(c2ccc(O)c(C)c2)(c2ccc(OCC(=O)C(C)(C)C)c(C)c2)CC1
1-{4-[1-Acetyl-4-(4-hydroxy-3-methylphenyl)-piperidin-4-yl]-2-methylphenoxy}-3,3-dimethylbutan-2-one
CC(=O)N1CCC(c2ccc(O)c(C)c2)(c2ccc(OCC(=O)C(C)(C)C)c(C)c2)CC1
1-{4-[1-acetyl-4-(4-hydroxy-3-methylphenyl)-piperidin-4-yl]-2-methylphenoxy)-3,3-dimethylbutan-2-one
CC(C)(C)C(=O)CCl
1-chloropinacolone
OC[C@H]1CO1
(S)-glycidol
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherwas prepared

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07863298B2uspto-grants-2011_01