Triethylamine → HCID 86757778, compound

Participants

Reaction Steps

A solution of intermediate 15 (0.01 mol), 1-(4-phenyl-4-piperidinylcarbonyl)pyrrolidine hydrochloride (0.01 mol) and triethylamine (0.015 mol) in THF (10 ml) and titanium(IV)isopropoxide (3.72 ml) was stirred at RT for 4 hours. Ethanol (10 ml) and sodium cyanoborohydride (0.01 mol) were added. The mixture was stirred for a few hours. Ice and ethanol (10 ml) were added and the mixture was stirred at RT for 30 minutes and then filtered over decalite. The solvent was evaporated and the residue extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by HPLC over silica gel (eluent: CH2Cl2/CH3OH 95/5). Two pure fractions were collected and their solvents were evaporated. The residue was crystallized from DIPE. The precipitate was filtered off and dried, yielding 4.07 g of (±)-cis-1-[3,5-bis(trifluoromethyl)-benzoyl]-4-[4-phenyl-4-(1-pyrrolidinylcarbonyl)-1-piperidinyl]-2-[[4-(trifluoromethyl)-phenyl]methyl]piperidine (55%) (compound 111) and 1.3 g of (±)-trans-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[4-phenyl-4-(1-pyrrolidinylcarbonyl)-1-piperidinyl]-2-[[4-(trifluoromethyl)phenyl]methyl]-piperidine (18%) (compound 112).

Provenance & Evidence