Sodium hydride → Tert-butyl 4-[2-(2-iodo-4-nitrophenoxy)ethyl]piperidine-1-carboxylate

HRID 542005

Reaktionsgleichung

Reaktionsgleichung von HRID 542005
[H-].[Na+].[OH:3][CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.F[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:21]=1[I:29]>O1CCCC1>[I:29][C:21]1[CH:22]=[C:23]([N+:26]([O-:28])=[O:27])[CH:24]=[CH:25][C:20]=1[O:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineHCID 105397331-Fluoro-2-iodo-4-nitrobenzene

Produkt 1

HCID 57962636Tert-butyl 4-[2-(2-iodo-4-nitrophenoxy)ethyl]piperidine-1-carboxylateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of sodium hydride (0.16 g, 3.9 mmol) in tetrahydrofuran (10 mL) at 0° C. was treated with a solution of tert-butyl 4-(2-hydroxyethyl)piperidine-1-carboxylate (0.82 mL, 3.7 mmol) in tetrahydrofuran (5 mL) and stirred at 0° C. for 30 minutes. The reaction mixture was treated with a solution of 1-fluoro-2-iodo-4-nitrobenzene (1.0 g, 3.7 mmol) in tetrahydrofuran (5 mL) and heated at 70° C. for 16 h. The reaction mixture was concentrated, diluted with ethyl acetate, and washed with water. The aqueous layer was separated and extracted with additional ethyl acetate. The combined organic extracts were washed with brine, dried with sodium sulfate, filtered, and concentrated to a crude brown oil. Purification by flash column chromatography gave the desired product (1.4 g, 81%) as a yellow oil. LCMS for C18H251N2O5Na (M+Na)+: m/z=499.0.

Aufarbeitung

  1. temperatureheated at 70° C. for 16 h
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. customThe aqueous layer was separated
  6. extractionextracted with additional ethyl acetate
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to a crude brown oil
  11. customPurification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f3958cb0ed554b0182c77a915e97325f
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871753B2

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