Acetone → HCID 69285620, compound

Participants

Reaction Steps

Examples 11p and 11q, Step 6: To a solution of 2-((1S,2S,5R)-5-amino-2-(dibenzylamino)cyclohexyl)acetonitrile (4.35 mmoles) in 40 ml of anhydrous dichloroethane was added acetone (3.5 ml), and the mixture was stirred for 30 minutes at room temperature. Then sodium triacetoxyborohydride (3 g) was added, and the mixture was stirred for 1.5 hours. To the mixture was added 37% aqueous formaldehyde (2.2 ml) and it was stirred for 15 minutes. Then additional 1.6 g of sodium triacetoxyborohydride was added, and the mixture was continued to stir for 2.5 hours. At the end of the stirring, was added saturated Na2CO3, and the product was extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and evaporated to give an oily residue. It was purified by column chromatography (silica gel, 0.5:4.5:95 cNH4OH-MeOH—CH2Cl2) to give 1 g of ((1S,2S,5R)-2-(dibenzylamino)-5-(isopropyl(methyl)amino)cyclohexyl)acetonitrile as an oil.

Provenance & Evidence