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

HRID 389916Notes

Reaction equation

HRID 389916 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[CH2:16][CH2:15][CH2:14][N+:13]2([CH3:27])[CH:17](C2C=NC=CN=2)[C:18](=[O:20])[NH2:19])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[Br-].[OH:36][C@@H:37]1[CH2:41][CH2:40][N+:39](C)(C(C2C=NC=CN=2)C(=O)N)C1.[Br-].O[C@@H]1CC[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[CH2:16][CH2:15][CH2:14][N+:13]2([CH2:17][C:18](=[O:20])[NH:19][C:40]2[CH:41]=[CH:37][O:36][N:39]=2)[CH3:27])=[O:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 131730241(1R/S,3R)-3-Hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-pyrrolidinium bromide2×HCID 131730243(R/S)-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-methyl-1-(pyrazin-2-yl-carbamoylmethyl)-pyrrolidinium bromideHCID 131730247(1R/S,3R)-3-hydroxy-1-methyl-1-(pyrazin-2-yl-carbamoylmethyl)-pyrrolidinium bromide

Product 1

HCID 131730245(R/S)-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-(isoxazol-3-ylcarbamoyl-methyl)-1-methyl-pyrrolidinium bromide

Procedure

This compound is prepared by an analogous method to (1R/S,3R)-3-((R/S)-(2-cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-methyl-1-(pyrazin-2-ylcarbamoylmethyl)-pyrrolidinium bromide (Example 1) by replacing (1R/S,3R)-3-hydroxy-1-methyl-1-(pyrazin-2-yl-carbamoylmethyl)-pyrrolidinium bromide (Intermediate B) with (1R/S,3R)-3-hydroxy-1-(isoxazol-3-ylcarbamoyl-methyl)-1-methyl-pyrrolidinium bromide (Intermediate D).

Sources & evidence

ORD record
ord-1e7e88cc66f344c483ca03f65ddea787
Source dataset
uspto-grants-2013_02
Patent number
US08383625B2

Reaction notes

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