4-Hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide → 4-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide

HRID 1690649Notes

Reaction equation

HRID 1690649 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]CC2CCC[N+]2(C(C2C=CON=2)C(=O)N)C)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[Br-].O[CH2:37][C@H:38]1[CH2:42][CH2:41][CH2:40][N+:39]1([CH2:44][C:45](=[O:52])[NH:46][C:47]1[CH:51]=[CH:50][O:49][N:48]=1)[CH3:43].[Br-].OC1CC[N+](CC(=O)NC2C=CON=2)(C)CC1>>[Br-:1].[CH:2]1([C:8]([OH:34])([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:9]([O:11][CH:42]2[CH2:37][CH2:38][N+:39]([CH2:44][C:45](=[O:52])[NH:46][C:47]3[CH:51]=[CH:50][O:49][N:48]=3)([CH3:43])[CH2:40][CH2:41]2)=[O:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 871979834-Hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide2×HCID 131729615(1R/S,2R)-2-Hydroxymethyl-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-pyrrolidinium bromideHCID 131729617(R/S)-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxymethyl)-1-(isoxazol-3-yl carbamoylmethyl)-1-methyl-pyrrolidinium bromide

Product 1

HCID 871979054-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide

Procedure

This compound is prepared by an analogous method to (1R/S,2R)-2-((R/S)-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxymethyl)-1-(isoxazol-3-yl carbamoylmethyl)-1-methyl-pyrrolidinium bromide (Example 1) by replacing (1R/S,2R)-2-hydroxymethyl-1-(isoxazol-3-ylcarbamoyl-methyl)-1-methyl-pyrrolidinium bromide (Intermediate B) with 4-hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide (Intermediate I).

Sources & evidence

ORD record
ord-4fb766a87d244ab8b0968c29a095eba7
Source dataset
uspto-grants-2012_04
Patent number
US08153669B2

Reaction notes

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