9-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-9-aza-6-azoniaspiro[4.5]decane chloride → 4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one

HRID 2281337Notes

Reaction equation

HRID 2281337 reaction equation
[Cl-].[OH:2][C@H:3]([C:15]1[CH:24]=[CH:23][C:18]2[C:19](=[O:22])[O:20][CH2:21][C:17]=2[C:16]=1[CH3:25])[CH2:4]N1CC2(CCCC2)[NH2+]CC1>C(O)C>[CH3:25][C:16]1[C:17]2[CH2:21][O:20][C:19](=[O:22])[C:18]=2[CH:23]=[CH:24][C:15]=1[C@@H:3]1[CH2:4][O:2]1

Participants

3

Reactant 1

HCID 1176420669-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-9-aza-6-azoniaspiro[4.5]decane chloride2×

Product 1

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1 (3H)-one (INTERMEDIATE 2) (38 mg, 0.20 mmol) in 0.50 mL of ethanol was prepared. Separately, 9-[(2R)-2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-9-aza-6-azoniaspiro[4.5]decane Chloride (INTERMEDIATE 3)(60. mg, 0.20 mmol) was dissolved in 1 mL of ethanol by addition of 200 mg of MP-CO3 resin and heating. The two solutions, along with the resin, were combined and microwaved at 140° C. for fifty-five minutes. The solvent was removed in vacuo and the remaining solids were dissolved in 1 mL DMSO.

Workup

  1. temperatureheating
  2. custommicrowaved at 140° C. for fifty-five minutes
  3. customThe solvent was removed in vacuo
  4. dissolutionthe remaining solids were dissolved in 1 mL DMSO

Sources & evidence

ORD record
ord-874d8403a5254000a1bbd116546e505a
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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