2-Bromo-1,2-diphenylethan-1-one → 2-Oxo-1,2-diphenylethyl 1-(3-benzyloxybenzoyl)-2-piperidinecarboxylate

HRID 380128

Reaktionsgleichung

[Na].[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=1)[C:13]([N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[C:21]([OH:23])=[O:22])=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:27]1([C:33]([CH:35](Br)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)C.S(=O)(=O)(O)O>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=1)[C:13]([N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[C:21]([O:23][CH:35]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:33](=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:22])=[O:14])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

Sodium (54 mg) was dissolved in ethanol (8.0 ml), and then 1-(3-benzyloxybenzoyl)-2-piperidinecarboxylic acid (665 mg), conc. sulfuric acid (1 drop), and desyl bromide (539 mg) was successively dissolved thereto. The resulting mixture was stirred at 70° C. for 2 days, cooled to room temperature, and partitioned between ethyl acetate and 1N HCl. The organic layer was washed with 1N HCl, aqueous sodium bicarbonate, and brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed over silica gel to afford 2-oxo-1,2-diphenylethyl 1-(3-benzyloxybenzoyl)-2-piperidinecarboxylate (297 mg) as a pale yellow oil.

Aufarbeitung

temperaturecooled to room temperature
custompartitioned between ethyl acetate and 1N HCl
washThe organic layer was washed with 1N HCl, aqueous sodium bicarbonate, and brine
dry with materialdried over MgSO4
customevaporated in vacuo
customThe residue was chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag: ord-969536c747cd4b3a94fb701bec284060
Quelldatensatz: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06300344B1

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