Reaktion #2048774

Reaktionsgleichung

5-Cyano-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide

5-cyano-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide

benzyl chloride

lithium hexamethyldisilazide

→

5-benzyl-5-cyano-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide

Ausbeute 46.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 4 hours
2. 2
   Sonstigequenched with 50 mL of water
3. 3
   ExtraktionThe mixture was extracted with ethyl acetate
4. 4
   TrocknenThe combined organic extracts were dried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe resulting residue was purified by silica gel column chromatography

Vorschrift

5-Cyano-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 12a (4.0 g, 19.3 mmol) was dissolved in 60 mL of tetrahydrofuran with stirring followed by addition of benzyl chloride (5.4 g, 42.5 mmol) and lithium hexamethyldisilazide (42.5 mL, 42.5 mmol) under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 4 hours. The reaction was monitored by TLC until the disappearance of the starting materials and quenched with 50 mL of water. The mixture was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 5-benzyl-5-cyano-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 14a (2.6 g, yield 46%) as a light yellow solid.

Quelle