Ethyl Acetate → 1-(2-nitrobenzyl)pyrrolidine

HRID 226455Notes

Reaction equation

HRID 226455 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>CN(C=O)C.[Cl-].[Na+].O>[N+:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 31268PyrrolidineHCID 77569alpha-Bromo-2-nitrotolueneHCID 81531Diisopropylethylamine

Product 1

HCID 2643101-(2-nitrobenzyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 1-(bromomethyl)-2-nitrobenzene (2.10 g) in DMF (20 mL) was added pyrrolidine (0.95 mL) and N,N-diisopropylethylamine (2.54 mL), and the mixture was stirred at 60° C. for 24 hours. The resulting mixture was poured into ethyl acetate and brine. The organic phase was separated and washed with brine, dried over sodium sulfate. The solvent was evaporated in vacuo and the residue was purified by silica gel column chromatography to give 1-(2-nitrobenzyl)pyrrolidine (1.92 g) as a pale yellow oil.

Workup

  1. customThe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-80aaec1e8f5348f69886c049856eb1c0
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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