N-Iodosuccinimide → HCID 12083025, Verbindung

HRID 1168500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1168500
[OH:1][CH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[I:22]N1C(=O)CCC1=O>CN(C=O)C>[OH:1][CH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([I:22])[CH:9]=2)[N:4]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 2776402Benzyl 2-(Hydroxymethyl)-1-Indolinecarboxylate

Produkt 1

HCID 12083025HCID 12083025, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution containing benzyl 2-(hydroxymethyl)-1-indolinecarboxylate (Preparation 6, 1.78 g), N-iodosuccinimide (2.83 g), and anhydrous DMF (12 mL) is stirred overnight at 60° C. in a foil-covered flask. This solution is cooled and concentrated to half volume with a stream of nitrogen. The resulting brown solution is partitioned between water (50 mL) and CH2Cl2 (150 mL). The organic phase is washed with brine, dried (Na2SO4), filtered, and concentrated to give a brown oil. The crude product is chromatographed eluting with 0-40% EtOAc in heptane (300 mL each 10%) to give 2.03 g (79%) of the title compound as a peach solid. Physical characteristics: M.p. 110-111° C.; HRMS (FAB) m/z 410.0270 (C17H16INO3+H). Anal. Found: C, 49.83; H, 3.95; N, 3.37.

Aufarbeitung

  1. temperatureThis solution is cooled
  2. concentrationconcentrated to half volume with a stream of nitrogen
  3. customThe resulting brown solution is partitioned between water (50 mL) and CH2Cl2 (150 mL)
  4. washThe organic phase is washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a brown oil
  9. customThe crude product is chromatographed
  10. washeluting with 0-40% EtOAc in heptane (300 mL each 10%)

Quellen und Nachweise

ORD-Eintrag
ord-6d3878d2ff2d4878bed7de02de17e0d9
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06624159B2

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