Sodium hydride → HCID 86612986, compound

HRID 1012114Notes

Reaction equation

HRID 1012114 reaction equation
[H-].[Na+].[C:3]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][OH:18])[CH2:12][CH2:11]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[N+:19]([C:22]1[CH:23]=[C:24](F)[CH:25]=[CH:26][C:27]=1[N+:28]([O-:30])=[O:29])([O-:21])=[O:20]>C1COCC1.C(OCC)(=O)C>[C:6]([O:5][C:3]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][O:18][C:24]2[CH:25]=[CH:26][C:27]([N+:28]([O-:30])=[O:29])=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)[CH2:12][CH2:11]1)=[O:4])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2986753,4-DinitrofluorobenzeneHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Product 1

HCID 86612986HCID 86612986, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 0.096 g, 2.4 mmol) was added in several portions to a solution of N-Boc-4-piperidine ethanol (0.550 g, 2.4 mmol) in THF (20 ml). To this mixture was added a solution of 3,4-dinitrofluorobenzene (0.372 g, 2.0 mmol) and the resultant mixture was stirred at ambient temperature for 16 h. The reaction mixture was diluted with ethyl acetate (100 ml), washed with water (60 ml) and the aqueous phase back extracted with ethyl acetate (3×50 ml). The combined organics were washed with brine (50 ml), dried (MgSO4) and reduced in vacuo. The resulting residue was subjected to column chromatography eluting with a 0-50% gradient of ethyl acetate in petroleum ether. 4-[2-(3,4-dinitro-phenoxy)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester was obtained as a yellow oil (0.361 g, 46%).

Workup

  1. washwashed with water (60 ml)
  2. extractionthe aqueous phase back extracted with ethyl acetate (3×50 ml)
  3. washThe combined organics were washed with brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. washeluting with a 0-50% gradient of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-e1bfdf24422149f3aadbfa78dd007f0a
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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