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

HRID 248888Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 248888
[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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 14995339(1RS)-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-yl]-2,2,2-trifluoroethanolAusbeute 24,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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:

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-45d7cb3e577943959cd79a7f8d380ef0
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05212191

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