Triethylamine → 5-Oxo-8-propionyl-1,2,3,5-tetrahydroindolizin-6-yl trifluoromethanesulfonate

HRID 253118

Reaktionsgleichung

Reaktionsgleichung von HRID 253118
[OH:1][C:2]1[C:3](=[O:15])[N:4]2[C:8](=[C:9]([C:11](=[O:14])[CH2:12][CH3:13])[CH:10]=1)[CH2:7][CH2:6][CH2:5]2.CCN(CC)CC.C1(N[S:30]([C:33]([F:36])([F:35])[F:34])(=[O:32])=[O:31])C=CC=CC=1>C(Cl)Cl>[F:34][C:33]([F:36])([F:35])[S:30]([O:1][C:2]1[C:3](=[O:15])[N:4]2[C:8](=[C:9]([C:11](=[O:14])[CH2:12][CH3:13])[CH:10]=1)[CH2:7][CH2:6][CH2:5]2)(=[O:32])=[O:31]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 668447316-hydroxy-8-propanoyl-2,3-dihydro-1H-indolizin-5-one

Produkt 1

HCID 866140165-Oxo-8-propionyl-1,2,3,5-tetrahydroindolizin-6-yl trifluoromethanesulfonateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred, cooled (0° C.) solution of 6-hydroxy-8-propionyl-2,3-dihydroindolizin-5-(1H)-one (1.10 g, 4.53 mmol) in CH2Cl2 (10 mL) was added Et3N. After stirring for 20 min., N-phenyltrifluoromethane sulfonamide was added in one portion. The mixture was stirred at RT for 6 h and quenched with H2O. the mixture was extracted with CH2Cl2 (3×) and the combined organic layers were dried over MgSO4, concentrated and purified by ISCO (40% EtOAc/Hexanes) to give the title compound as a white solid (1.50 g, 99%).

Aufarbeitung

  1. stirringThe mixture was stirred at RT for 6 h
  2. customquenched with H2O
  3. extractionthe mixture was extracted with CH2Cl2 (3×)
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. custompurified by ISCO (40% EtOAc/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9e63cb49188542f9b0af786c27090fc1
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872009B2

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