alpha-Cyclopentylmandelic acid → 4-((R)-2-Cyclopentyl-2-hydroxy-2-phenyl-acetoxy)-1-methyl-1-(3-phenyl-propyl)-piperidinium bromide

HRID 1690653Notes

Reaction equation

HRID 1690653 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)[CH2:7][CH2:6][CH2:5][CH2:4]C1.[Br-].OC[C@H]1CCC[N+]1(CC(=O)NC1C=CON=1)C.[Br-].[OH:54][CH:55]1[CH2:60][CH2:59][N+:58]([CH3:70])([CH2:61][CH2:62][CH2:63][C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[CH2:57][CH2:56]1.C1(C(C2C=CC=CC=2)(O)C(O)=O)CCCC1>>[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:54][CH:55]2[CH2:56][CH2:57][N+:58]([CH3:70])([CH2:61][CH2:62][CH2:63][C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)[CH2:59][CH2:60]2)=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 4

HCID 98283alpha-Cyclopentylmandelic acidHCID 669025494-Hydroxy-1-methyl-1-(3-phenyl-propyl)-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 669024124-((R)-2-Cyclopentyl-2-hydroxy-2-phenyl-acetoxy)-1-methyl-1-(3-phenyl-propyl)-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-ylcarbamoylmethyl)-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-methyl-1-(3-phenyl-propyl)-piperidinium bromide (Intermediate K) and by replacing cyclohexyl-hydroxy-phenyl-acetic acid with cyclopentyl-mandelic acid.

Sources & evidence

ORD record
ord-57d7f2700cce4da0846fe376c8428612
Source dataset
uspto-grants-2012_04
Patent number
US08153669B2

Reaction notes

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