Pentane → HCID 69286603, compound

Participants

Reaction Conditions

Reaction Steps

Examples 11p and 11q, Step 7: To a solution of 2-((1S,2S,5R)-2-(dibenzylamino)-5-(isopropyl(methyl)amino)cyclohexyl)acetonitrile (0.996 g, 2.56 mmoles) in 10 ml of anhydrous THF at −78° C. was added 0.7M-isopropyl lithium in pentane (5.5 ml, 3.84 mmoles) dropwise, and the mixture was stirred for 2.5 hours while the temperature was raised to −7° C. gradually. The reaction was quenched with saturated NH4Cl and then the solution was made basic with saturated NaHCO3. It was extracted with EtOAc (2×), and the combined extracts were washed with brine, dried over Na2SO4, and evaporated to give an oily residue. It was purified by flash chromatography (silica gel, 0.5:4.5:95 cNH4OH-MeOH—CH2Cl2) to give 0.73 g of 1-((1S,2S,5R)-2-(dibenzylamino)-5-(isopropyl(methyl)amino)cyclohexyl)-3-methylbutan-2-one.

Provenance & Evidence