(3R)-1-methylpiperidin-3-ol → (1R/S,3R)-3-Hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide

HRID 1690640Notes

Reaction equation

HRID 1690640 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([OH:8])[CH2:3]1.[Br:9][CH2:10][C:11]([NH:13][C:14]1[CH:18]=[CH:17][O:16][N:15]=1)=[O:12]>C(Cl)(Cl)Cl.C(#N)C>[Br-:9].[OH:8][C@@H:4]1[CH2:5][CH2:6][CH2:7][N+:2]([CH2:10][C:11](=[O:12])[NH:13][C:14]2[CH:18]=[CH:17][O:16][N:15]=2)([CH3:1])[CH2:3]1

Participants

4

Reactant 2

HCID 6994421(3R)-1-methylpiperidin-3-olHCID 133629192-bromo-N-(isoxazol-3-yl)acetamide2×

Product 1

HCID 87357711(1R/S,3R)-3-Hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-piperidinium bromide

Reagents, catalysts & solvents 1

HCID 22555007Acetonitrile chloroformSolvent

Procedure

(R)-1-Methyl-piperidin-3-ol (1.15 g, 10 mmol) and 2-bromo-N-isoxazol-3-yl-acetamide (Intermediate A) (2.25 g, 11 mmol) are stirred together in chloroform/acetonitrile (20 ml of a 1:1 mixture) at room temperature for 1 hour. The solvent is removed in vacuo and the resulting oil is purified using C-18 reverse phase column chromatography (eluent-water:acetonitrile from 0% to 30% acetonitrile) to yield the titled compound.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe resulting oil is purified

Sources & evidence

ORD record
ord-fbef3470ef174a01b4e955d0427f12ca
Source dataset
uspto-grants-2012_04
Patent number
US08153669B2

Reaction notes

Loading…