Triethylamine → 3-(3,3-Dimethylbutyl)-3-azabicyclo[3.1.0]hexane-6-carboxamide

Participants

Reaction Steps

The 3-azabicyclo[3.1.0]hexane-6-carboxamide hydrochloride (169 mg, 1.04 mmol) prepared in Example 5 and a molecular sieve were dried in vacuum and dissolved in 5 mL of methylene chloride. Then, triethylamine (151 μL, 1.08 mmol) was added dropwise at 0° C. After adding 3,3-dimethylbutyraldehyde (135 μL, 1.08 mmol), the mixture was stirred at room temperature for 1 hour. After adding sodium triacetoxyborohydride (687 mg, 3.24 mmol) and then adding 10 mL of methylene chloride, the mixture was stirred for 2 hours and 30 minutes. The completion of the reaction was confirmed by TLC (CH2Cl2:MeOH=10:1). After the reaction was completed, the reaction mixture was diluted with methylene chloride and extracted several times with saturated sodium bicarbonate. The organic layer was dried with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and separated by column chromatography (CH2Cl2:MeOH=10:1) to obtain 173 mg (79.2%) of the target compound.

Provenance & Evidence