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Tetrahydrofuran → Tert-butyl 4-cyano-4-(2-((methylsulfonyl)oxy)ethyl)piperidine-1-carboxylate

HRID 39705
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 39705
O1CCCC1.[C:6]([C:8]1([CH2:21][CH2:22][OH:23])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)#[N:7].[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C(N(CC)CC)C>[C:6]([C:8]1([CH2:21][CH2:22][O:23][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:10][CH2:9]1)#[N:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 60064207Tert-butyl 4-cyano-4-(2-hydroxyethyl)piperidine-1-carboxylate

Produkt 1

HCID 86617989Tert-butyl 4-cyano-4-(2-((methylsulfonyl)oxy)ethyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8471
Triethylamine
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 10 mL of a tetrahydrofuran solution containing 1.0 g of tert-butyl 4-cyano-4-(2-hydroxyethyl)piperidine-1-carboxylate, 0.77 mL of triethylamine was added at room temperature, thereto was added 0.37 mL of methane sulfonyl chloride under cooling with ice, and the mixture was stirred at the same temperature for 2 hours and 30 minutes. The reaction mixture was added with an aqueous saturated sodium hydrogen carbonate solution and ethyl acetate. The organic layer was separated, washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 1.3 g of a brown oily substance, tert-butyl 4-cyano-4-(2-((methylsulfonyl)oxy)ethyl)piperidine-1-carboxylate.

Aufarbeitung

  1. additionwas added at room temperature
  2. temperatureunder cooling with ice
  3. customThe organic layer was separated
  4. washwashed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9801021c71b64ca89316160c934c3309
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08524738B2

Notizen zur Reaktion

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