Tetrahydrofuran → HCID 18367412, compound

HRID 380091Notes

Reaction equation

HRID 380091 reaction equation
[C:1]1([C:7]2[N:8]=[C:9](C(O)C(CCO)CC3C=C(OC)C=CC=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(Cl)(=O)=O.[CH2:38]([N:40]([CH2:43][CH3:44])[CH2:41][CH3:42])[CH3:39].[CH2:45]1[CH2:49][O:48][CH2:47][CH2:46]1>C(OCC)(=O)C>[CH2:38]([N:40]1[CH2:43][CH2:44][CH:42]([CH2:17][C:12]2[CH:13]=[CH:46][CH:45]=[C:49]([O:48][CH3:47])[CH:11]=2)[CH:41]1[C:9]1[O:10][C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=1)[C:39]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18367238HCID 18367238, compound

Product 1

HCID 18367412HCID 18367412, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[3-(4,5-diphenyloxazol-2-yl)-3-hydroxy-2-(2-hydroxyethyl)propyl]-1-methoxybenzene (3.3 g) and methanesulfonyl chloride (1.8 ml) and triethylamine (4.3 ml) in THF (50 ml) was stirred at room temperature for 1 hour. 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 organic 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)-3-(3-methoxybenzyl)pyrrolidine (1.5 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. stirringAfter being stirred for 2 hours at 80° C.
  6. customthe mixture was partitioned between ether and water
  7. washThe organic layer was washed with water and brine
  8. customThe dried solvent was evaporated in vacuo
  9. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-fae8a1e1d4754210b73114ebbc35a487
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

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