Hydrochloric Acid → HCID 60123706, compound

HRID 2417244Notes

Reaction equation

HRID 2417244 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

In an atmosphere of nitrogen, phenylmagnesium bromide (3 N diethyl ether solution, 15 ml) was added dropwise to tetrahydrofuran solution (50 ml) of N-methyl-N-methoxy-1-[1-(R)-phenylethyl]-5-oxopyrrolidine-3-(R)-carboxamide (2.49 g, 9.0 mmol), and the mixture was stirred at room temperature for 30 minutes. The reaction solution was mixed with 1 N hydrochloric acid (50 ml) under ice-cooling and extracted with ethyl acetate (8 ml×2). The organic layer was washed with saturated brine (100 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure and the residue was subjected to a silica gel column chromatography. By eluting with n-hexane:ethyl acetate (1:1), 2.36 g (89%) of the title compound was obtained as a light yellow oil.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate (8 ml×2)
  3. washThe organic layer was washed with saturated brine (100 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under a reduced pressure
  6. washBy eluting with n-hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-f168abc1d3fa4c5bb7048ecbdcfe9ad1
Source dataset
uspto-grants-2004_11
Patent number
US06825353B2

Reaction notes

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