Reaktion #2294779

Reaktionsgleichung

7-(benzenesulfonyl)-8-(4-bromo-6-methyl-2-pyridyl)-3-methyl-3,9-diazaspiro[4.4]nonan-4-one

potassium tert-butoxide

acetic acid

→

racemic 2-(4-bromo-6-methyl-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe mixture was filtered
2. 2
   Waschenwashed with dichloromethane
3. 3
   Einengenthe filtrate concentrated at reduced pressure
4. 4
   Sonstigeto give a brown gum
5. 5
   SonstigeThe product was purified by silica gel chromatography
6. 6
   Wascheneluting with 40-100% ethyl acetate in iso-hexane

Vorschrift

To a solution of 7-(benzenesulfonyl)-8-(4-bromo-6-methyl-2-pyridyl)-3-methyl-3,9-diazaspiro[4.4]nonan-4-one (which may be prepared as described in Description 12) in THF (20 mL) at 00° C. was added 1.7 M potassium tert-butoxide in THF (2.69 mL, 4.58 mmol) dropwise over 5 minutes. The reaction mixture was stirred at 00° C. for 1.5 hours. The reaction was quenched by the addition of acetic acid (0.26 mL, 4.58 mmol) and then the mixture was filtered, washed with dichloromethane and the filtrate concentrated at reduced pressure to give a brown gum. The product was purified by silica gel chromatography eluting with 40-100% ethyl acetate in iso-hexane to give racemic 2-(4-bromo-6-methyl-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one a pale yellow solid (D13) (314 mg);

Quelle