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Cesium carbonate → 1,1-Dimethylethyl 4-[(4-nitro-2-pyridinyl)oxy]-1-piperidinecarboxylate

HRID 1993664
Notes
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Reaction equation

HRID 1993664 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][N:3]=1.[OH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([O:11][C:2]2[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][N:3]=2)[CH2:13][CH2:14]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 7351522-Chloro-4-nitropyridineHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphine

Product 1

HCID 685380211,1-Dimethylethyl 4-[(4-nitro-2-pyridinyl)oxy]-1-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalyst
HCID 1140TolueneSolvent

Procedure

Add 100 mL of toluene to a nitrogen purged mixture of 2-chloro-4-nitro-pyridine (4.32 g, 27.2 mmol), tert-butyl 4-hydroxypiperidine carboxylate (11.0 g, 54.5 mmol), cesium carbonate (13.3 g, 40.8 mmol), palladium acetate (122 mg, 0.544 mmol) and 2-(di-tert-butylphosphino)-1,1′-binapthyl (271 mg, 0.68 mmol). Stir the resulting mixture overnight at room temperature, then partition between water and ethyl acetate. Extract the aqueous layer with additional ethyl acetate, and dry the combined organic layer over sodium sulfate and concentrate under reduced pressure. Subject residue to silica gel chromatography eluting with a gradient of 0 to 20% ethyl acetate in hexanes to afford 4-(4-nitro-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester as a white waxy solid (5.37 g, 61%; LCMS ES+(m/z) 268 [M-tBu]+).

Workup

  1. custompurged
  2. custompartition between water and ethyl acetate
  3. extractionExtract the aqueous layer with additional ethyl acetate
  4. dry with materialdry the combined organic layer over sodium sulfate
  5. concentrationconcentrate under reduced pressure
  6. washSubject residue to silica gel chromatography eluting with a gradient of 0 to 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-aee9de94020a42c59a4939777f686770
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07652015B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes