Water → (R)-3-hydroxy-1-phenylpyrrolidin-2-one

HRID 2261478Notes

Reaction equation

HRID 2261478 reaction equation
[CH3:1][CH2:2][N:3]([CH:7]([CH3:9])C)[CH:4]([CH3:6])[CH3:5].S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=[O:11].N1C[CH2:28][CH2:27][CH2:26]1.[OH2:30]>C(Cl)Cl>[OH:30][C@@H:9]1[CH2:1][CH2:2][N:3]([C:4]2[CH:5]=[CH:28][CH:27]=[CH:26][CH:6]=2)[C:7]1=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531Diisopropylethylamine

Product 1

HCID 59593452(R)-3-hydroxy-1-phenylpyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of alcohol (4.64 mmol) and DIEA (11.59 mmol) in DCM (10 mL) at −20° C. was added triflic anhydride (5.56 mmol) and the reaction mixture was stirred at this temperature for 20 min. A solution of pyrrolidine (3.86 mmol) in DCM (6 mL) was added and the reaction mixture was stirred at −20° C. for 1 hour. The reaction mixture was poured into water and extracted with EtOAc (3×). The combined organic extracts were washed with water (2×), brine, dried (Na2SO4) and evaporated to dryness. Purification by silica gel chromatography afforded the desired product.

Workup

  1. stirringthe reaction mixture was stirred at −20° C. for 1 hour
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic extracts were washed with water (2×), brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-c262349734c3471fbdba3d59a7526958
Source dataset
uspto-grants-2010_12
Patent number
US07846954B2

Reaction notes

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