Hydrochloric Acid → HCID 60123706, compound

HRID 348395Notes

Reaction equation

HRID 348395 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(OC)[C:11]([C@@H:13]1[CH2:17][C:16](=[O:18])[N:15]([C@@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:20])[CH2:14]1)=[O:12].Cl>O1CCCC1>[C:1]1([C:11]([C@H:13]2[CH2:14][N:15]([C@@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:20])[C:16](=[O:18])[CH2:17]2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 20741434HCID 20741434, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 60123706HCID 60123706, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, phenylmagnesium bromide (3N diethyl ether solution, 15 ml) was added dropwise to a tetrahydrofuran solution (50 ml) of N-methyl-N-methoxy-1-[1-(R)-phenylethyl]-5-oxopyrrolidine-3-(R)-carboxamide (2.49 g, 9.0 mmol), followed by stirring at room temperature for 30 minutes. To the reaction solution was added 1 mol/l hydrochloric acid (50 ml) under ice cooling and the mixture was extracted with ethyl acetate (8 ml×2). The organic layer was washed with saturated saline (100 ml) and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was subjected to silica gel column chromatography. Elution with n-hexane/ethyl acetate (1/1) afforded the title compound (2.36 g, 89%) as a pale yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (8 ml×2)
  2. washThe organic layer was washed with saturated saline (100 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter removal of the solvent under reduced pressure
  5. washElution with n-hexane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-ac7b057d635b4ebc8cca86bf17b4bc4a
Source dataset
uspto-grants-2007_02
Patent number
US07176313B2

Reaction notes

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