StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Diisopropylamine → HCID 70050443, Verbindung

HRID 1720488
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1720488
C(NC(C)C)(C)C.[C:8]1([CH3:17])[CH:13]=[CH:12][C:11]([S@:14]([CH3:16])=[O:15])=[CH:10][CH:9]=1.[CH2:18]([O:25][C:26]([N:28]1[CH2:41][CH2:40][CH2:39][C@H:29]1[C:30]([N:32]1[CH2:38][CH2:37][CH2:36][C@H:33]1[CH:34]=[O:35])=[O:31])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>C1COCC1>[CH2:18]([O:25][C:26]([N:28]1[CH2:41][CH2:40][CH2:39][C@H:29]1[C:30]([N:32]1[CH2:38][CH2:37][CH2:36][C@H:33]1[CH:34]([OH:35])[CH2:16][S@@:14]([C:11]1[CH:12]=[CH:13][C:8]([CH3:17])=[CH:9][CH:10]=1)=[O:15])=[O:31])=[O:27])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 122623Benzyl 2-(2-formylpyrrolidine-1-carbonyl)pyrrolidine-1-carboxylateHCID 11170275(S)-(-)-Methyl p-tolyl sulfoxide

Produkt 1

HCID 70050443HCID 70050443, VerbindungAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To diisopropylamine (0.26 ml) in THF (6 ml) was dropwise added 1.62M n-butyllithium-hexane solution (1.12 ml) at -78° C., and the mixture was stirred at 0° C. for 0.5 hour. The reaction mixture was cooled to -30° C., dropwise added with (S)-(-)-methyl p-tolyl sulfoxide (255 mg) in THF (6 ml), and stirred at 0° C. for 0.5 hour. The reaction mixture was cooled to -78° C. and dropwise added with known N-benzyloxycarbonyl-L-prolyl-L-prolinal (300 mg) in THF (6 ml). After stirring for 0.5 hour, an aqueous solution of saturated ammonium chloride was added thereto, followed by stirring at room temperature for 10 minutes. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine order, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluate; chloroform-methanol) to give 388 mg of the title compound.

Aufarbeitung

  1. customat -78° C.
  2. temperatureThe reaction mixture was cooled to -30° C.
  3. stirringstirred at 0° C. for 0.5 hour
  4. temperatureThe reaction mixture was cooled to -78° C.
  5. stirringAfter stirring for 0.5 hour
  6. stirringby stirring at room temperature for 10 minutes
  7. extractionThe reaction mixture was extracted with ethyl acetate
  8. washthe organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine order
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel column chromatography (eluate; chloroform-methanol)

Quellen und Nachweise

ORD-Eintrag
ord-3e6f706c851e499eb3d97ef7385fee51
Quelldatensatz
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05506256

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion