((2R)-1-methylpyrrolidin-2-yl)methanol → (1R/S,2R)-2-Hydroxymethyl-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-pyrrolidinium bromide

HRID 1690639Notes

Reaction equation

HRID 1690639 reaction equation
[Br:1][CH2:2][C:3]([NH:5][C:6]1[CH:10]=[CH:9][O:8][N:7]=1)=[O:4].[CH3:11][N:12]1[CH2:16][CH2:15][CH2:14][C@@H:13]1[CH2:17][OH:18]>C(#N)C>[Br-:1].[OH:18][CH2:17][C@H:13]1[CH2:14][CH2:15][CH2:16][N+:12]1([CH2:2][C:3](=[O:4])[NH:5][C:6]1[CH:10]=[CH:9][O:8][N:7]=1)[CH3:11]

Participants

4

Reactant 2

HCID 11007868((2R)-1-methylpyrrolidin-2-yl)methanolHCID 133629192-bromo-N-(isoxazol-3-yl)acetamide2×

Product 1

HCID 131729615(1R/S,2R)-2-Hydroxymethyl-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-pyrrolidinium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 2-bromo-N-isoxazol-3-yl-acetamide (Intermediate A) (3.9 g, 191 mmol) in acetonitrile (95 ml) is added ((R)-1-methyl-pyrrolidin-2-yl)-methanol (2.2 g, 191 mmol) in acetonitrile (5 ml). The reaction mixture is stirred at room temperature for 3 hours and then the solvent is removed in vacuo. The resulting oil is taken up in acetonitrile and ethyl acetate is then added. The resulting cloudy solution is stirred at room temperature for 30 minutes. There after, the supernatant is decanted off and the solid is dried under vacuum over two days to afford the titled compound.

Workup

  1. customthe solvent is removed in vacuo
  2. additionethyl acetate is then added
  3. stirringThe resulting cloudy solution is stirred at room temperature for 30 minutes
  4. customThere after, the supernatant is decanted off
  5. customthe solid is dried under vacuum over two days

Sources & evidence

ORD record
ord-3afe382844e44c5daf037742318bd4e8
Source dataset
uspto-grants-2012_04
Patent number
US08153669B2

Reaction notes

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