Hydrochloric Acid → (S)-3-[(R)-1-(2,4,5-Trifluorophenoxy)penyl]pyrrolidine

HRID 587999

Reaktionsgleichung

Reaktionsgleichung von HRID 587999
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([C@H:13]([OH:18])[CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9]1)=O)(C)(C)C.CN(C=O)C.[H-].[Na+].[F:26][C:27]1[CH:32]=[C:31]([F:33])[C:30]([F:34])=[CH:29][C:28]=1F.Cl.[CH3:37]CO>>[F:26][C:27]1[CH:32]=[C:31]([F:33])[C:30]([F:34])=[CH:29][C:28]=1[O:18][C@@:13]1([C@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH2:37]1

Komponenten

7

Edukt 6

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6228DimethylformamideHCID 94741,2,4,5-TetrafluorobenzeneHCID 24758Sodium hydride2×HCID 58104597(S)-3-((R)-1-Hydroxypentyl)pyrrolidine-1-carboxylic acid t-butyl ester

Produkt 1

HCID 131734426(S)-3-[(R)-1-(2,4,5-Trifluorophenoxy)penyl]pyrrolidine

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(S)-3-((R)-1-Hydroxypentyl)pyrrolidine-1-carboxylic acid t-butyl ester (40.0 mg, 155 μmol) was dissolved in DMF (100 mL, 12.9 mmol). While stirring, 60% sodium hydride in oil (0.4:0.6, sodium hydride:mineral oil, 18.6 mg, 311 μmol) was slowly added, and the mixture was stirred for 15 minutes. 1,2,4,5-Tetrafluorobenzene (52.1 μL, 466 μmol) was added. The mixture was then heated at 90° C. for 3 hours. The reaction was quenched with MeOH (1 mL), and the solvent was removed under reduced pressure. 1.25M HCl in EtOH (2.0 mL, 2.5 mmol) was added, and the mixture was stirred overnight. The product was concentrated and purified by preparative HPLC to yield the title compound as a mono-TFA salt (19.2 mg, 97% purity). MS m/z: [M+H]+ calcd for C15H20F3NO, 288.15. found 288.2.

Aufarbeitung

  1. stirringthe mixture was stirred for 15 minutes
  2. customThe reaction was quenched with MeOH (1 mL)
  3. customthe solvent was removed under reduced pressure
  4. stirringthe mixture was stirred overnight
  5. concentrationThe product was concentrated
  6. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3d761ede706f44de9a5291bc2d04358e
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227933B2

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