Methanol → HCID 6933979, compound

HRID 270115Notes

Reaction equation

HRID 270115 reaction equation
C(N(CC)CC)C.O[N:9]1[C:13](=O)C2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].[CH2:20]([C@@H:22]1[O:24][CH2:23]1)Cl.C[OH:26].[O:27]1[CH2:32][CH2:31][O:30]CC1>>[OH:27][C@@H:32]1[CH2:31][O:30][N:9]([C:10]([C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:20]=2[C:22]([O:24][CH3:23])=[O:26])=[O:19])[CH2:13]1

Participants

6

Reactant 5

HCID 887MethanolHCID 8471Triethylamine3×HCID 10665N-HydroxyphthalimideHCID 312751,4-DioxaneHCID 2734062(-)-Epichlorohydrin2×

Product 1

HCID 6933979HCID 6933979, compound

Conditions

Temperature
50 °C

Procedure

Triethylamine (0.28 ml) was added to a solution of N-hydroxyphthalimide (5.00 g, 30 mmol) and (R)-(−)-epichlorohydrin (2.40 ml, 30.6 mmol) in anhydrous dioxane (10 ml) under nitrogen. The mixture was stirred at 50° C. for 48 h, further (2R)-2-(chloromethyl)oxirane (0.24 ml) and triethylamine (0.28 ml) were added and stirring continued at 50° C. for 24 h. Methanol (10 ml) and further triethylamine (4.27 ml) were added and stirring continued at 50° C. for 2 h. The mixture was evaporated under reduced pressure, the residue dissolved in saturated aqueous sodium bicarbonate solution (100 ml) and extracted with ethyl acetate (6×100 ml). Combined organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was recrystallised from ethyl acetate to give the sub-title compound (3.4 g).

Workup

  1. stirringstirring
  2. waitcontinued at 50° C. for 24 h
  3. stirringstirring
  4. waitcontinued at 50° C. for 2 h
  5. customThe mixture was evaporated under reduced pressure
  6. dissolutionthe residue dissolved in saturated aqueous sodium bicarbonate solution (100 ml)
  7. extractionextracted with ethyl acetate (6×100 ml)
  8. dry with materialCombined organic extracts were dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated under reduced pressure
  11. customThe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-f83460dee3004fa98cef96c33aff5768
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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