Reaktion #2294777

Reaktionsgleichung

3-amino-1-methyl-pyrrolidin-2-one

4-bromo-3-methyl-pyridine-2-carbaldehyde

phenyl vinyl sulfone

calcium triflate

phenyl vinyl sulfone

calcium triflate

triethylamine

Triethylamine

→

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

Ausbeute 26.5%

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

Ausbeute 26.5%

Lösungsmittel

methanol

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction was stirred for 15 minutes
2. 2
   Sonstigeto precipitate out of the reaction
3. 3
   Sonstigethis was sonicated
4. 4
   workup.STIRRINGstirred for a further 15 minutes
5. 5
   FiltrationThe solid was then filtered off
6. 6
   Waschenwashed with additional methanol (approximately 10 mL)
7. 7
   WaschenThe pale cream solid was then washed with diethyl ether (10 mL), and air
8. 8
   Sonstigedried for 10 minutes
9. 9
   Sonstigeto give a colourless solid
10. 10
    workup.STIRRINGThe reaction mixture was then stirred at room temperature for 16 hours
11. 11
    FiltrationThe solid was filtered off
12. 12
    Waschenwashed with Et2O (10 mL)
13. 13
    Sonstigeair dried for 15 minutes on the sinter

Vorschrift

To a stirred solution of 3-amino-1-methyl-pyrrolidin-2-one (3258.49 mg, 28.55 mmol) in methanol (8 mL) was added 4-bromo-3-methyl-pyridine-2-carbaldehyde (which may be prepared as described in Description 7) (5710 mg, 28.55 mmol), phenyl vinyl sulfone (4801.68 mg, 28.55 mmol), and calcium triflate (482.74 mg, 1.43 mmol). The reaction was stirred for 5 minutes. Triethylamine (3.97 mL, 28.55 mmol) was then added [caution—slight exotherm observed], and the reaction was stirred for 15 minutes. A large amount of solid was observed to precipitate out of the reaction, this was sonicated and stirred for a further 15 minutes. The solid was then filtered off, and washed with additional methanol (approximately 10 mL). The pale cream solid was then washed with diethyl ether (10 mL), and air dried for 10 minutes to give a colourless solid, then dissolved in MeOH (8 mL), and treated with phenyl vinyl sulfone (4801.68 mg, 28.55 mmol), calcium triflate (482.74 mg, 1.43 mmol) and lastly triethylamine (3.97 mL, 28.55 mmol). The reaction mixture was then stirred at room temperature for 16 hours. The solid was filtered off, and washed with Et2O (10 mL). The solid was then air dried for 15 minutes on the sinter to afford 7-(benzene-sulfonyl)-8-(4-bromo-3-methyl-2-pyridyl)-3-methyl-3,9-diazaspiro[4.4]nonan-4-one (D8) (3520 mg, 7.58 mmol, 26.5% yield);

Quelle