Benzilic acid → (1R/S,3R)-3-(2-Hydroxy-2,2-diphenyl-acetoxymethyl)-1-(isoxazol-3-ylcarbamoyl methyl)-1-methyl-piperidinium bromide

HRID 1690655Notes

Reaction equation

[Br-:1].[CH:2]1([C:8]([OH:34])([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][N+:13]2([CH2:19][C:20](=[O:27])[NH:21][C:22]2[CH:26]=[CH:25][O:24][N:23]=2)[CH3:18])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C:35](O)(=O)C(C1C=CC=CC=1)(C1C=CC=CC=1)O>>[Br-:1].[OH:34][C:8]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([O:11][CH2:12][C@@H:17]1[CH2:16][CH2:15][CH2:14][N+:13]([CH2:19][C:20](=[O:27])[NH:21][C:22]2[CH:26]=[CH:25][O:24][N:23]=2)([CH3:35])[CH2:18]1)=[O:10]

Participants

Reactant 2

HCID 6463Benzilic acid

HCID 131729619(R/S)-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-(isoxazol-3-ylcarbamoyl-methyl)-1-methyl-piperidinium bromide

Product 1

HCID 131729623(1R/S,3R)-3-(2-Hydroxy-2,2-diphenyl-acetoxymethyl)-1-(isoxazol-3-ylcarbamoyl methyl)-1-methyl-piperidinium bromide

Procedure

This compound is prepared by an analogous method (1R/S,2R)-3-((R/S)-(2-cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide: (Example 2) by replacing cyclohexyl-hydroxy-phenyl-acetic acid with benzilic acid.

Sources & evidence

ORD record: ord-23cfc3dfbb454a188a1b5359f2f2de37
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153669B2

Reaction notes

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