Ethanol → HCID 16006725, compound

HRID 2355838Notes

Reaction equation

HRID 2355838 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)[CH2:9][N:10]2[CH:14](OCC)[CH2:13][CH2:12][C:11]2=O)=[CH:4][CH:3]=1.[CH2:27](O)[CH3:28]>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[C:19]3[C:24](=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH2:12][CH2:11][N:10]4[CH2:28][CH2:27][CH2:5][CH2:8][CH2:9]4)[CH:20]=3)[C@H:11]3[CH2:12][CH2:13][CH2:14][N:10]3[CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 67542885HCID 67542885, compound

Product 1

HCID 16006725HCID 16006725, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-[2-(4-bromo-phenyl)-2-(3-methoxy-phenyl)-ethyl]-5-ethoxy-pyrrolidin-2-one (472.2 mg, 1.13 mmol) and MSA (2 N in ethanol, 10 mL) was stirred for 2 h at rt. The mixture was diluted with EtOAc, washed with satd. aq. NaHCO3 and brine, dried (MgSO4), and concentrated to give a colorless oil. Chromatographic purification (EtOAc/hexanes) yielded 325.4 mg (78%) of the desired product as a mixture of cis and trans diastereomers. The diastereomers were separated by normal-phase HPLC.

Workup

  1. washwashed with satd
  2. dry with materialaq. NaHCO3 and brine, dried (MgSO4)
  3. concentrationconcentrated
  4. customto give a colorless oil
  5. customChromatographic purification (EtOAc/hexanes)

Sources & evidence

ORD record
ord-6e71cd376cd2402585ece266ab95168f
Source dataset
uspto-grants-2010_07
Patent number
US07754882B2

Reaction notes

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