alpha-Bromo-2-nitrotoluene → HCID 54074348, compound

HRID 2355918Notes

Reaction equation

HRID 2355918 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[N+:29]([C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34]Br)([O-:31])=[O:30]>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1([CH2:34][C:33]2[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=2[N+:29]([O-:31])=[O:30])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 77569alpha-Bromo-2-nitrotolueneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

Product 1

HCID 54074348HCID 54074348, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (8.23 g, 0.032 mol) in tetrahydrofuran (85 mL) was slowly added a solution of sodium bis(trimethylsilyl)amide (44 mL, 0.044 mol). After the resulting mixture had been stirred at −78° C. for 1 h, a solution of 2-nitrobenzyl bromide (8.21 g, 0.038 mol) was added. The reaction mixture was allowed to warm up to room temperature and was stirred overnight. It was then concentrated and the residue was partitioned between water and ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The final product was purified from the complex reaction mixture by way of column chromatography on silica gel (eluent-hexanes-ethyl acetate 4:1) to give the desired product (1.61 g, 13%) as brown oil. Mass spec.: 415.38 (M+Na)+.

Workup

  1. temperatureto warm up to room temperature
  2. stirringwas stirred overnight
  3. concentrationIt was then concentrated
  4. customthe residue was partitioned between water and ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe final product was purified from the complex reaction mixture by way of column chromatography on silica gel (eluent-hexanes-ethyl acetate 4:1)

Sources & evidence

ORD record
ord-86bb3ff1f18044098c0945d686d64a3e
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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