Tributylstannane → 4-Benzoyloxy-1-t-butoxy-2,2,6,6-tetramethylpiperidine

HRID 1590945

Reaktionsgleichung

Reaktionsgleichung von HRID 1590945
[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[N:13]([OH:18])[C:12]([CH3:20])([CH3:19])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21](I)([CH3:24])([CH3:23])[CH3:22].C([SnH](CCCC)CCCC)CCC>ClC1C=CC=CC=1>[C:1]([O:9][CH:10]1[CH2:11][C:12]([CH3:20])([CH3:19])[N:13]([O:18][C:21]([CH3:24])([CH3:23])[CH3:22])[C:14]([CH3:16])([CH3:17])[CH2:15]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 5948TributylstannaneHCID 112062-Iodo-2-methylpropaneHCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

Produkt 1

HCID 129969074-Benzoyloxy-1-t-butoxy-2,2,6,6-tetramethylpiperidineAusbeute 44,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Versuchsvorschrift

A solution of 56.0 g (203 mmol) of 4-benzoyloxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 125 ml of chlorobenzene, and 58.9 g of t-butyl iodide is cooled to 5° C. Tri-n-butyltin hydride (29 g, 100 mmol) is added dropwise over 110 minutes while the temperature is maintained below 20° C. The reaction mixture is concentrated at reduced pressure and then purified by silica gel chromatography (200:1, then 100:3 heptane:ethyl acetate) to afford 30.1 g of a white solid, m.p. 80°-82.5° C.

Aufarbeitung

  1. temperatureis maintained below 20° C
  2. concentrationThe reaction mixture is concentrated at reduced pressure
  3. custompurified by silica gel chromatography (200:1

Quellen und Nachweise

ORD-Eintrag
ord-03b8a0f652b34942ad38273eb81f18a7
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05204473

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