Ammonium Chloride → 5-Cyano-5-cyclohexylmethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide

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.

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

ORD record

ord-c4f9db3dfd5b4d71962d65860258e421

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304411B2