Reaktion #1960718

Reaktionsgleichung

cyclohexylmethyl bromide

lithium hexamethyldisilazide

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

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

ammonium chloride

→

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

Ausbeute 41.5%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was reacted at room temperature for 2 hours
2. 2
   ExtraktionThe mixture was extracted with ethyl acetate (60 mL×3)
3. 3
   TrocknenThe combined organic extracts were dried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe resulting residue was purified by silica gel column chromatography

Vorschrift

5-Cyano-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 12a (3.66 g, 17.6 mmol) was dissolved in 150 mL of tetrahydrofuran with stirring followed by dropwise addition of cyclohexylmethyl bromide (6.2 g, 35.2 mmol) and lithium hexamethyldisilazide (35.2 mL, 32.5 mmol). The reaction mixture was reacted at room temperature for 2 hours. The reaction was monitored by TLC until the disappearance of the starting materials. Then 150 mL of a saturated aqueous solution of ammonium chloride was added. The mixture was extracted with ethyl acetate (60 mL×3). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 5-cyano-5-cyclohexylmethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 15a (2.2 g, yield 41.5%) as a yellow solid.

Quelle