1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-5-ol;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The octahydro-5-hydroxycyclopenta[c]pyrrol hydrochloride (44.4 mmol) prepared in the step 1 was dissolved in 100 ml of acetonitrile, and 4.91 ml (44.4 mmol) of 1,2-difluoro-4-nitrobenzene and 23.20 ml (133.2 mmol) of N,N-diisopropylethylamine were added, and the mixture was heat to reflux for 6 hours. After the reaction was completed, the temperature was lowered to room temperature, and the mixture was concentrated under reduced pressure to remove the solvent. The solvent-free concentrate was dissolved in ethyl acetate, and washed with distilled water, and then, the organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound, of which NMR data is as follow. the mixture was heat to reflux for 6 hours was lowered to room temperature the mixture was concentrated under reduced pressure to remove the solvent The solvent-free concentrate was dissolved in ethyl acetate washed with distilled water the organic layer was dried over magnesium sulfate filtered concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10.00 g (44.4 mmol) of 5-oxo-hexahydro-cyclopenta[c]pyrrol-2-carboxylic acid tert-butyl ester (Hanchem Co. Ltd.) was dissolved in 100 ml of methanol, the temperature was lowered to 0° C., 3.36 g (88.8 mmol) of sodium borohydride was added, and then, the mixture was stirred for 1 hour. And, 15 ml of an aqueous solution of concentrated hydrochloric acid (35% (v/v)) was slowly added, and the mixture was additionally stirred for 1 hour, and then, the solvent was removed under reduced pressure to obtain the title compound. was lowered to 0° C. the mixture was additionally stirred for 1 hour the solvent was removed under reduced pressure