Methanol → HCID 86675622, compound

HRID 1844576Notes

Reaction equation

HRID 1844576 reaction equation
C(=O)/C=C/CC.[C:7]1([C:13]([C:24]2C=CC=CC=2)(O[Si](C)(C)C)[C@@H:14]2CCC[NH:15]2)C=CC=C[CH:8]=1.[CH:30](OC)([O:33][CH3:34])[O:31][CH3:32].[OH2:37].C1(C)C=CC(S(O)(=O)=O)=CC=1.C[OH:50]>[N+](C)([O-])=O>[CH3:32][O:31][CH:30]([O:33][CH3:34])[CH2:24][C@H:13]([CH2:14][N+:15]([O-:50])=[O:37])[CH2:7][CH3:8]

Participants

7

Reactant 5

HCID 887MethanolHCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 5364752(E)-2-PentenalHCID 11198150(S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol Trimethylsilyl Ether

Product 1

HCID 86675622HCID 86675622, compound

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

Nitromethane (4.33 mL) was added to a solution of trans-2-pentenal (2.27 g) and (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine (Org. Lett., 2007, vol. 9, p. 5307) (920 mg) in methanol (54 mL) with stirring at room temperature. The mixture was stirred at room temperature for 4 days. Then, trimethyl orthoformate (17.7 mL) and p-toluenesulfonic acid monohydrate (1.03 g) were added to the reaction solution, and the mixture was further stirred overnight. The reaction solution was concentrated, and a saturated aqueous solution of sodium bicarbonate was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution and then dried over anhydrous sodium sulfate. Filtration and concentration under reduced pressure were performed to obtain the title compound (4.81 g).

Workup

  1. stirringThe mixture was stirred at room temperature for 4 days
  2. concentrationThe reaction solution was concentrated
  3. additiona saturated aqueous solution of sodium bicarbonate was added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-d1f7c95a0ca44a2289414dd77f13e44e
Source dataset
uspto-grants-2015_02
Patent number
US08946443B2

Reaction notes

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