Triethylamine → HCID 18367229, compound

HRID 380117Notes

Reaction equation

HRID 380117 reaction equation
O[CH:2]([C:7]1[O:8][C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1)[CH2:3][CH2:4][CH2:5]O.CS(Cl)(=O)=O.C([N:31]([CH2:34][CH3:35])CC)C>O1CCCC1.C(OCC)(=O)C>[CH2:34]([N:31]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:7]1[O:8][C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1)[C:35]1[CH:5]=[CH:4][CH:3]=[CH:2][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18367433HCID 18367433, compound

Product 1

HCID 18367229HCID 18367229, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(1,4-dihydroxybutyl)-4,5-diphenyloxazole (1 g) in tetrahydrofuran (10 ml) were added methanesulfonyl chloride (1.6 g) and triethylamine (1.5 ml) at 0° C. The solution was diluted with ethyl acetate and washed with sat. NaHCO3 and brine, dried over MgSO4, and evaporated. The residue was dissolved in benzylamine (10 ml). After being stirred for 2 hours at 80° C., the mixture was partitioned between ether and water. The or-ganic layer was washed with water and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to afford 1-benzyl-2-(4,5-diphenyloxazol-2-yl)pyrrolidine (1.3 g).

Workup

  1. washwashed with sat. NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. dissolutionThe residue was dissolved in benzylamine (10 ml)
  5. customthe mixture was partitioned between ether and water
  6. washThe or-ganic layer was washed with water and brine
  7. customThe dried solvent was evaporated in vacuo
  8. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-6fe6ab96180f468e9c8ae339092dbe6e
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

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