Hydrochloric Acid → HCID 60123706, compound

HRID 457403Notes

Reaction equation

HRID 457403 reaction equation
[C:1]1([Mg])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OCC)C.CN(OC)[C:15]([C@@H:17]1[CH2:21][C:20](=[O:22])[N:19]([C@@H:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH3:24])[CH2:18]1)=[O:16].Cl>O1CCCC1>[C:1]1([C:15]([C@H:17]2[CH2:18][N:19]([C@@H:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH3:24])[C:20](=[O:22])[CH2:21]2)=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 20741434HCID 20741434, compoundHCID 178507003HCID 178507003, compound

Product 1

HCID 60123706HCID 60123706, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an atmosphere of nitrogen, phenylmagnesium bride (3 mol/l diethyl ether solution, 15 ml) was added dropwise to tetrahydrofuran solution (50 ml) of N-methyl-N-methoxy-[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 mol/l hydrochloric acid (50 ml) under ice-cooling and then extracted with ethyl acetate (8 ml×2). The organic layer was washed with saturated brine (100 ml) and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure and the resulting residue was applied 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-e22c873530b94a3c9600a13f39fbf1c9
Source dataset
uspto-grants-2007_03
Patent number
US07186843B2

Reaction notes

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