2-Bromoethanol → 4-Piperidineacetic acid

HRID 1989879Notes

Reaction equation

BrCCO.Cl.C1([CH:12]([CH:16]2[CH2:21][CH2:20][N:19](C3C=CC(NC(C4C=CC=CC=4C4C=CC(C(F)(F)F)=CC=4)=O)=CC=3)[CH2:18][CH2:17]2)[C:13]([OH:15])=[O:14])C=CC=CC=1>CN(C=O)C>[NH:19]1[CH2:20][CH2:21][CH:16]([CH2:12][C:13]([OH:15])=[O:14])[CH2:17][CH2:18]1

Participants

Conditions

Temperature: 70 °C

Procedure

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).

Workup

customThe solvent was evaporated
customThe residue was partitioned between water and DCM
customThe extract's solvent was evaporated
customThe residue was purified by HPLC (Waters column
customCH3CN (0 minutes) 85/15, (10 minutes) 10/90, (16 minutes) 0/100, (18.10-20.00 minutes) 85/15
customThe product fractions were collected
customthe organic solvent was evaporated
extractionThe aqueous concentrates were extracted
customthe extract's solvent was evaporated

Sources & evidence

ORD record: ord-515b2ec2bac4444ea853a0d8809e944e
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642378B2

Reaction notes

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