Carbon Dioxide → HCID 69926904, Verbindung

HRID 1280752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1280752
[F:1][CH:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([OH:5])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)=O.C(N(CC)CC)C.FC(F)(F)C(O)=O.[NH:43]1[CH2:47][CH2:46][C@@H:45]([S:48][C:49]2[CH:54]=[CH:53][C:52]([OH:55])=[CH:51][CH:50]=2)[CH2:44]1>CN(C=O)C>[F:1][CH:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([N:43]1[CH2:47][CH2:46][C@@H:45]([S:48][C:49]2[CH:54]=[CH:53][C:52]([OH:55])=[CH:51][CH:50]=2)[CH2:44]1)=[O:5]

Komponenten

7

Edukt 5

HCID 280Carbon DioxideHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 9812939HCID 9812939, VerbindungHCID 69924259HCID 69924259, Verbindung

Produkt 1

HCID 69926904HCID 69926904, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

(RS)-2-Fluoro-4-phenyl-butyric acid (0.66 g, 3.63 mmol) was dissolved in DMF (5 ml) and carbonyldiimidazole (0.64 g, 3.8 mmol) was added portionwise. After evolution of CO2 has ceased, the reaction mixture was warmed to 55° C. for 20 minutes and then cooled to room temperature. A mixture of triethylamine (0.46 ml, 3.3 mmol) and (3R)-4-(pyrrolidin-3-ylsulfanyl)-phenol trifluoroacetic acid (1.02 g, 3.3 mmol) in DMF (5 ml) was added. The mixture was stirred at room temperature for 2 hours. The solvent was removed in vacuo and the residue taken up in H2O (30 ml).The mixture was extracted with ethylacetate (3×20 ml). The combined organic phases were dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was chromatographed over silica gel (CH2Cl2—MeOH, 99:1) to provide (2RS,3R)-2-fluoro-1-[3-(4-hydroxy-phenylsulfanyl)-pyrrolidin-1-yl]-4-phenyl-butan-1-one (1.12 g, 95%) as light yellow oil, MS: m/e=359.1(M+).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. additionwas added
  3. customThe solvent was removed in vacuo
  4. extractionwas extracted with ethylacetate (3×20 ml)
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customThe residue was chromatographed over silica gel (CH2Cl2—MeOH, 99:1)

Quellen und Nachweise

ORD-Eintrag
ord-a6ce16e2ccac4297b92bc16b472b3772
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451819B2

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