Cesium carbonate → Methyl 1-(4-(methoxycarbonyl)-2-nitrophenyl)piperidine-2-carboxylate

HRID 576502Notes

Reaction equation

F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[C:21]([O:23][CH3:24])=[O:22].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][C:2]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]2[C:21]([O:23][CH3:24])=[O:22])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1)=[O:7]

Participants

Conditions

Temperature: 55 °C

Procedure

To a mixture of methyl 4-fluoro-3-nitrobenzoate (6.46 g, 32.5 mmole) and methyl piperidine-2-carboxylate (5.57 g, 1.2 equiv) in DMF (80 mL) was added Cs2CO3 (1.2.7 g). The reaction mixture was stirred at 55° C. overnight. The solid was filtered and the filtrate was evaporated. The residue was recrystallized with EtOAc/Hexane to give Methyl 1-(4-(methoxycarbonyl)-2-nitrophenyl)piperidine-2-carboxylate (9.4 g, 90%).

Workup

filtrationThe solid was filtered
customthe filtrate was evaporated
customThe residue was recrystallized with EtOAc/Hexane

Sources & evidence

ORD record: ord-f30d0ad2661b429e9862c3477d9dda6d
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040508B2

Reaction notes

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