Tetrahydrofuran → HCID 18367412, compound

HRID 1741358Notes

Reaction equation

HRID 1741358 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). MS (m/z): 501 (M+ +1) IR (Neat): 1600 cm-1NMR (CDCl3, δ): 2.0-3.2 (7H, m), 3.60 (3H, s), 3.5-4.0 (3H, m), 6.5-6.8 (3H, m), 7.0-7.8 (16H, m)

Workup

  1. washwashed with sat. NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. customand evaporated
  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-facff1ed9a7543e0a0524dfd60469ec8
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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