2-bromo-N-(isoxazol-3-yl)acetamide → (1R/S,3R)-3-Hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-pyrrolidinium bromide

HRID 389913Notes

Reaction equation

HRID 389913 reaction equation
[Br-].[OH:2][CH:3]1[CH2:7][CH2:6][N@@+:5]([CH3:18])([CH2:8][C:9](=[O:17])[NH:10][C:11]2[CH:16]=NC=C[N:12]=2)[CH2:4]1.[Br:19]C[C:21](NC1C=NC=CN=1)=[O:22].BrCC(NC1C=CON=1)=O>>[Br-:19].[OH:2][C@@H:3]1[CH2:7][CH2:6][N+:5]([CH2:8][C:9](=[O:17])[NH:10][C:11]2[CH:16]=[CH:21][O:22][N:12]=2)([CH3:18])[CH2:4]1

Participants

4

Reactant 3

HCID 133629192-bromo-N-(isoxazol-3-yl)acetamide2×HCID 445426692-bromo-N-(pyrazin-2-yl)acetamideHCID 87282153(R)-3-hydroxy-1-methyl-1-(pyrazin-2-ylcarbamoylmethyl)-pyrrolidinium bromide2×

Product 1

HCID 131730241(1R/S,3R)-3-Hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-pyrrolidinium bromide

Procedure

This compound is prepared by a method that is analogous to that used to prepare (R)-3-hydroxy-1-methyl-1-(pyrazin-2-ylcarbamoylmethyl)-pyrrolidinium bromide (Intermediate B) by replacing 2-Bromo-N-pyrazin-2-yl-acetamide (Intermediate A) with 2-Bromo-N-isoxazol-3-yl-acetamide (Intermediate C).

Workup

  1. customThis compound is prepared by a method that

Sources & evidence

ORD record
ord-36af485f94ba4fa0a18b5b8df8a8ac26
Source dataset
uspto-grants-2013_02
Patent number
US08383625B2

Reaction notes

Loading…