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o-Xylyl bromide → HCID 54269290, Verbindung

HRID 443234
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 443234
[CH2:1]([O:8][C:9](=[O:23])[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:34][C:35]1[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=1[CH2:37]Br>C1COCC1>[CH2:1]([O:8][C:9](=[O:23])[C:10]1([CH2:34][C:35]2[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=2[CH3:37])[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:14][CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6992o-Xylyl bromideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 222559134-Benzyl 1-tert-butyl piperidine-1,4-dicarboxylate

Produkt 1

HCID 54269290HCID 54269290, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of N-t-butoxycarbonyl isonipecotic acid benzyl ester (13.34 g, 41.8 mmol) in THF (100 ml) at -78° C. was added sodium bis-trimethysilylamide (59 ml of a 1.0M THF solution, 59 mmol) over 15 min. The resulting orange solution was stirred at -78° C. for 1 hr and then treated dropwise with 2-methyl benzyl bromide (6.80 ml, 50.7 mmol) and then allowed to warm slowly to room temperature over 16 hrs. The reaction was quenched with saturated aqueous NH4Cl, diluted with H2O, and extracted with EtOAc. The combined organic extracts were washed with brine, and concentrated in vacuo to an orange gum. Chromatography (SiO2, gradient elution, 20 to 30% EtOAc in hexanes) afforded the product as a white solid.

Aufarbeitung

  1. temperatureto warm slowly to room temperature over 16 hrs
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. additiondiluted with H2O
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. concentrationconcentrated in vacuo to an orange gum
  7. washChromatography (SiO2, gradient elution, 20 to 30% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3f86b495e78d414e9d67fe7e77d71d30
Quelldatensatz
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05891889

Notizen zur Reaktion

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