2-Nitrophenol → Tert-butyl 4-(2-nitrophenoxy)piperidine-1-carboxylate

HRID 1093561Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27](OS(C)(=O)=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C.O>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([O:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 2-nitrophenol (1.5 g, 0.0101 mole) in DMF (15 mL) was added cesium carbonate (16.4 g, 0.0505 mole) followed by 4-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (3.0 g, 0.0101 mole). The reaction mixture was heated at 80° C. overnight. The mixture was then diluted with water and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with brine solution, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography using silica gel 60-120 mesh (20% ethyl acetate in hexane) to afford 1.5 g (47%) of 4-(2-nitro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester. LCMS: 323.15 (M+1)+, 98%,

Workup

extractionthe product was extracted with ethyl acetate
washThe ethyl acetate layer was washed with brine solution
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record: ord-08affbcb798d4f889f31b6c19a9c4c80
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129376B2

Reaction notes

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