(1R/S,3R)-3-Hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide → (R/S)-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-(isoxazol-3-ylcarbamoyl-methyl)-1-methyl-piperidinium bromide

HRID 1690648Notes

Reaction equation

HRID 1690648 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][CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][N+:14]2([CH:19](C2C=CON=2)[C:20](=[O:22])[NH2:21])[CH3:18])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[Br-].OC[C@H]1CCC[N+]1(CC(=O)N[C:47]1[CH:51]=[CH:50][O:49][N:48]=1)C.[Br-].O[C@@H]1CCC[N+](CC(=O)NC2C=CON=2)(C)C1>>[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:12]2[CH2:13][CH2:17][CH2:16][CH2:15][N+:14]2([CH2:19][C:20](=[O:22])[NH:21][C:47]2[CH:51]=[CH:50][O:49][N:48]=2)[CH3:18])=[O:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 87357711(1R/S,3R)-3-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 131729619(R/S)-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-(isoxazol-3-ylcarbamoyl-methyl)-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 (1R/S,2R)-3-Hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide (Intermediate C).

Sources & evidence

ORD record
ord-14df2af0cc9a48a0aa2f634686f19e17
Source dataset
uspto-grants-2012_04
Patent number
US08153669B2

Reaction notes

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