Reaktion #1960702

Reaktionsgleichung

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

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

iodomethane

lithium hexamethyldisilazide

→

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

Ausbeute 53.9%

Lösungsmittel

tetrahydrofuran

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was reacted for 2 hours until MS
2. 2
   Extraktionextracted with ethyl acetate (200 mL×3)
3. 3
   TrocknenThe combined organic extracts were dried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   Sonstigeto obtain an oil
7. 7
   Sonstigethe oil was purified by silica gel column chromatography

Vorschrift

5-Cyano-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 12a (4.2 g, 20.2 mmol) and iodomethane (11.5 g, 80.8 mmol) were dissolved in 100 mL of tetrahydrofuran followed by dropwise addition of lithium hexamethyldisilazide (80.8 mL, 80.8 mmol) at room temperature under nitrogen atmosphere. The reaction mixture was reacted for 2 hours until MS showed the disappearance of the starting materials. The mixture was diluted with 100 mL of water and extracted with ethyl acetate (200 mL×3). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain an oil. TLC showed that there are two adjacent spots, and then the oil was purified by silica gel column chromatography to obtain the bottom spot compound 5-cyano-5-methyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 12b (2.411 g) as a light yellow oil.

Quelle