Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 21978759, compound

HRID 10173Notes

Reaction equation

HRID 10173 reaction equation
O1CCCCC1[O:7][CH2:8][C:9]1[CH2:13][CH:12]([CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[O:11][N:10]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[N:15]1([CH2:14][CH:12]2[O:11][N:10]=[C:9]([CH2:8][OH:7])[CH2:13]2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21978771[5-((Morpholin-4-yl)methyl)-4,5-dihydro-isoxazol-3-yl]methyl 2-tetrahydropyranyl ether

Product 1

HCID 21978759HCID 21978759, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [5-((morpholin-4-yl)methyl)-4,5-dihydro-isoxazol-3-yl]methyl 2-tetrahydropyranyl ether (0.63 g) with pyridinium p-toluenesulfonate (10 mol %) in methanol was heated under reflux for 24 h. After cooling to room temperature the solvent was removed in vacuo and the residue purified by flash chromatography (SiO2, CH2Cl2/MeOH/NH4OH 92/7.5/0.5) to afford [5-((morpholin-4-yl)methyl)-4,5-dihydro-isoxazol-3-yl]methanol (95%). Rf 0.17 (CH2Cl2/MeOH/NH4OH 92/7.5/0.5).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 h
  3. customwas removed in vacuo
  4. customthe residue purified by flash chromatography (SiO2, CH2Cl2/MeOH/NH4OH 92/7.5/0.5)

Sources & evidence

ORD record
ord-d64a33a850374f16bffd91ecddd6d0c9
Source dataset
uspto-grants-2006_08
Patent number
US07094779B2

Reaction notes

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