alpha-Cyclopentylmandelic acid → (R/S)-(2-Cyclopentyl-2-hydroxy-2-phenyl-acetoxy)-1-methyl-1-(pyridazin-3-yl-carbamoylmethyl)-pyrrolidinium bromide

HRID 389920Notes

Reaction equation

HRID 389920 reaction equation
[Br-:1].[CH:2]1([C:8]([OH:34])([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30]C=2)[C:9]([O:11][CH:12]2[CH2:16][CH2:15][CH2:14][N+:13]2([CH3:27])[CH:17]([C:21]2[N:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:18](=[O:20])[NH2:19])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C1(C(C2C=CC=CC=2)(O)C(O)=O)CCCC1>>[Br-:1].[CH:28]1([C:8]([OH:34])([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([O:11][CH:12]2[CH2:16][CH2:15][CH2:14][N+:13]2([CH3:27])[CH:17]([C:21]2[N:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:18](=[O:20])[NH2:19])=[O:10])[CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

3

Reactant 2

HCID 98283alpha-Cyclopentylmandelic acidHCID 131730249(R/S)-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-methyl-1-(pyridazin-3-yl-carbamoylmethyl)-pyrrolidinium bromide

Product 1

HCID 131730255(R/S)-(2-Cyclopentyl-2-hydroxy-2-phenyl-acetoxy)-1-methyl-1-(pyridazin-3-yl-carbamoylmethyl)-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-(pyridazin-3-ylcarbamoylmethyl)-pyrrolidinium bromide (Example 3) by replacing cyclohexyl-hydroxy-phenyl-acetic acid with cyclopentyl-mandelic acid.

Sources & evidence

ORD record
ord-9ea769a3342a4866a598bccfd33fce4f
Source dataset
uspto-grants-2013_02
Patent number
US08383625B2

Reaction notes

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