HCID 69043248, compound → HCID 59318452, compound

HRID 1021068Notes

Reaction equation

HRID 1021068 reaction equation
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH:8]2[N:12]([C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C:11](=[O:19])[C:10](C)([C:20](O)=O)[CH2:9]2)=[CH:3][CH:2]=1>C1(C)C=CC=CC=1>[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@H:8]2[N:12]([CH2:13][N:12]3[CH2:8][CH2:9][CH2:10][CH2:11]3)[C:11](=[O:19])[C@H:10]([CH3:20])[CH2:9]2)=[CH:5][CH:6]=1.[C:1]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@H:8]2[N:12]([C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C:11](=[O:19])[C@@H:10]([CH3:20])[CH2:9]2)=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 69043248HCID 69043248, compound

Product 2

HCID 59318452HCID 59318452, compoundHCID 68714094HCID 68714094, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

63 mg (3R/S, 5R)-5-Biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-3-methyl-2-oxo-pyrrolidine-3-carboxylic acid (R1=Piv; R10=OH; R11=Me) [65:35.ratio of C3 isomers] is added to 25 ml toluene. The resulting mixture is heated to reflux and stirred for 16 h. The mixture is then cooled to room temperature and washed successively with 10 ml aqueous sodium hydrogen carbonate, brine and water. The organic phase is dried (MgSO4) and concentrated in vacuo to afford (3R,5S)-5-biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-3-methylpyrrolidin-2-one (2-a, R1=pivaloyl) and (3S,5S)-5-biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-3-methylpyrrolidin-2-one (2-b, R1=pivaloyl) as a 55:45 diastereomer mixture, respectively, according to the H NMR spectrum.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux
  3. washwashed successively with 10 ml aqueous sodium hydrogen carbonate, brine and water
  4. dry with materialThe organic phase is dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f54dc52d0afd405c9a767f12d3f49c73
Source dataset
uspto-grants-2014_05
Patent number
US08716495B2

Reaction notes

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