2-Bromoethanol → 4-Piperidineacetic acid

Participants

Reaction Conditions

Reaction Steps

2-Bromoethanol (1.2 equiv, 0.00010 mol) was added to a mixture of intermediate (24) (0.000084 mol) in DMF (5 ml) and CsCO3 (0.00018 mol) and the reaction mixture was stirred for 3 hours at 70° C. The solvent was evaporated. The residue was partitioned between water and DCM. The extract's solvent was evaporated. The residue was purified by HPLC (Waters column, with Xterra MS C18; eluent: [(0.5% NH4OAc in H2O)/CH3CN 90/10)]/CH3CN (0 minutes) 85/15, (10 minutes) 10/90, (16 minutes) 0/100, (18.10-20.00 minutes) 85/15). The product fractions were collected and the organic solvent was evaporated. The aqueous concentrates were extracted and the extract's solvent was evaporated, yielding 4-piperidineacetic acid, α-phenyl-1-[4-[[[4′-(trifluoromethyl)[1,1′-biphenyl]-2-yl]carbonyl]amino]phenyl]-, 2-hydroxyethyl ester (compound 134).

Provenance & Evidence