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m-Xylyl bromide → HCID 21193326, Verbindung

HRID 1068457
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1068457
[C:1]([O:5][C:6]([N:8]1[CH2:23][CH2:22][CH:11]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:34][C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=1)[CH2:38]Br>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH2:34][C:35]2[CH:42]=[CH:41][CH:40]=[C:37]([CH3:38])[CH:36]=2)([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:22][CH2:23]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 12099m-Xylyl bromideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 222559134-Benzyl 1-tert-butyl piperidine-1,4-dicarboxylate

Produkt 1

HCID 21193326HCID 21193326, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a cold (−78° C.) solution of benzyl N-tert-butoxycarbonyl-isonipecotate (8.02 g, 25.11 mmol) in anhydrous THF (80 mL), a solution of sodium bis(trimethysilyl)amide (35 mL, 35 mmol; 1 M) in THF was added over a period of 10 min. The resulting orange solution was stirred at −78° C. for 1 h. and then treated dropwise with 3-methylbenzyl bromide (4.1 mL, 30.6 mmol). The reaction mixture was allowed to warm to room temp., and stirred overnight. The reaction was quenched with saturated aqueous ammonium chloride, diluted with water, and extracted with ethyl acetate. The organic extracts were combined, washed with brine, and concentrated under vacuum. The residual oil was subjected to column chromatography on silica eluting with 20% ethyl acetate in hexane. Collection and concentration of appropriate fractions provided the title product.

Aufarbeitung

  1. temperatureto warm to room temp.
  2. stirringstirred overnight
  3. customThe reaction was quenched with saturated aqueous ammonium chloride
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. concentrationconcentrated under vacuum
  8. customCollection and concentration of appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-0dbf9857b43f46cf88a4b576182fb71c
Quelldatensatz
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06248756B1

Notizen zur Reaktion

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