Hydrochloric Acid → (1RS)-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-yl]-2,2,2-trifluoroethanol

HRID 248888Notes

Reaction equation

HRID 248888 reaction equation
[F:1][C:2]([F:5])([F:4])I.[CH2:6]([N:13]([CH3:27])[C:14]([CH2:16][CH2:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH:25]=[O:26])=[O:19])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl>[Zn].CN(C=O)C>[CH2:6]([N:13]([CH3:27])[C:14]([CH2:16][CH2:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH:25]([OH:26])[C:2]([F:5])([F:4])[F:1])=[O:19])=[O:15])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 16843TrifluoroiodomethaneHCID 14674666(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-al

Product 1

HCID 14995339(1RS)-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-yl]-2,2,2-trifluoroethanolYield 24.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

Trifluoroiodomethane (2.3 g) was cooled to -78° C. with a trap. DMF (7 ml), (2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-al (710 mg) and zinc (1.0 g) were added there to. And the mixture was treated with ultrasonic waves for 2 hrs. at room temperature. 1N hydrochloric acid was added to the reaction solution. The mixture was extracted with EtOAc. The extract was washed, dried, and evaporated. The residue was purified by column chromatography on silica gel (hexane-EtOAc) to give the title compound (217 mg) having the following physical data:

Workup

  1. additionAnd the mixture was treated with ultrasonic waves for 2 hrs
  2. customat room temperature
  3. extractionThe mixture was extracted with EtOAc
  4. washThe extract was washed
  5. customdried
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel (hexane-EtOAc)

Sources & evidence

ORD record
ord-45d7cb3e577943959cd79a7f8d380ef0
Source dataset
uspto-grants-1993_05
Patent number
US05212191

Reaction notes

Loading…