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o-Xylyl bromide → HCID 54269290, Verbindung

HRID 1068414
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1068414
[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 1.0 M 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-2c0de00953e74274a67d25d903d67a07
Quelldatensatz
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06248756B1

Notizen zur Reaktion

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