Methyl 3-bromopropanoate → Methyl 3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionate

HRID 13857

Reaktionsgleichung

Br[CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].[NH:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15](=[O:29])[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:10][CH2:9]1.CCN(C(C)C)C(C)C>C(#N)C>[CH3:7][O:6][C:4](=[O:5])[CH2:3][CH2:2][N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15](=[O:29])[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:12][CH2:13]1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

Methyl 3-bromopropionate (553 μL, 5.07 mmol) was added to a stirred solution of biphenyl-2-ylcarbamic acid piperidin-4-yl ester (1.00 g, 3.38 mmol; prepared as described in Preparation 1) and DIPEA (1.76 mL, 10.1 mmol) in ACN (34 mL) at 50° C. and the reaction mixture was heated at 50° C. overnight. The solvent was then removed under reduced pressure, and the residue was dissolved in DCM (30 mL). The resulting solution was washed with saturated aqueous sodium bicarbonate solution (10 mL), dried over MgSO4, filtered and the solvent was removed under reduced pressure. The crude residue was purified by column chromatography (5-10% MeOH/DCM) to give 905 mg of the title intermediate (70% yield).

Aufarbeitung

customThe solvent was then removed under reduced pressure
dissolutionthe residue was dissolved in DCM (30 mL)
washThe resulting solution was washed with saturated aqueous sodium bicarbonate solution (10 mL)
dry with materialdried over MgSO4
filtrationfiltered
customthe solvent was removed under reduced pressure
customThe crude residue was purified by column chromatography (5-10% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag: ord-d5ce28f4093644dea52f9b79850cc92e
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07728144B2

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