Trifluoroacetic acid → (S)-5-[(Biphenyl-4-yl)methyl]pyrrolidin-2-one

HRID 1021052Notes

Reaction equation

HRID 1021052 reaction equation
C(OC([N:8]1[C@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:11][CH2:10][C:9]1=[O:26])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:17]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:16]=[CH:15][C:14]([CH2:13][C@H:12]2[NH:8][C:9](=[O:26])[CH2:10][CH2:11]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 46193436(S)-2-biphenyl-4-ylmethyl-5-oxopyrrolidine-1-carboxylic acid t-butyl ester

Product 1

HCID 58160438(S)-5-[(Biphenyl-4-yl)methyl]pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8.9 g of (S)-5-biphenyl-4-ylmethyl-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (1-a, R1=BOC) (25.3 mmol) is dissolved in 90 ml methylene chloride. Then 5 ml CF3COOH are added. This mixture is stirred at it for 1.5 h. The reaction mixture is concentrated. Heptane fraction is then added to the residue. The product is crystallized. The obtained product is dissolved in toluene and then it is washed with NaHCO3 (aq) solution. The organic layer is evaporated to yield (S)-5-biphenyl-4-ylmethylpyrrolidin-2-one [Key Lactam (1-a, R1=H)]. Spectroscopic data as in Example 3.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additionHeptane fraction is then added to the residue
  3. customThe product is crystallized
  4. dissolutionThe obtained product is dissolved in toluene
  5. washit is washed with NaHCO3 (aq) solution
  6. customThe organic layer is evaporated

Sources & evidence

ORD record
ord-bb9f5f096eec4e9fbc66a15a1ce525b4
Source dataset
uspto-grants-2014_05
Patent number
US08716495B2

Reaction notes

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