Diisopropylethylamine → HCID 20725686, compound

HRID 1167449Notes

Reaction equation

HRID 1167449 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.C(N(CC)C(C)C)(C)C.[C:21]([O:25][C:26]([NH:28][C@@H:29]1[CH2:33][CH2:32][NH:31][CH2:30]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:31]1[CH2:32][CH2:33][C@@H:29]([NH:28][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[CH2:30]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine

Product 1

HCID 20725686HCID 20725686, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,4-Difluoronitrobenzene (16.03 g, 0.101 M) was dissolved in acetonitrile (300 ml), and treated with N,N-diisopropylethylamine (32.63 g, 0.253 M) and (3R)-3-t-butoxycarbonylaminopyrrolidine (20.65 g, 0.111 M). The mixture was stirred and heated to reflux for 18 hours. Solvent was evaporated, and the residue treated with EtOAc (300 ml) and water (200 ml). The organic laver was washed with water (1 50 ml). citric acid solution (10% in water, 2×150 ml), and dried (magnesium sulfate). Evaporation gave the desired product as a yellow solid (32.7 g), of sufficient quality for use without purification. MS (ESP): 326 (MH+) for C15H20FN3O4.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. customSolvent was evaporated
  4. additionthe residue treated with EtOAc (300 ml) and water (200 ml)
  5. washThe organic laver was washed with water (1 50 ml)
  6. dry with materialcitric acid solution (10% in water, 2×150 ml), and dried (magnesium sulfate)
  7. customEvaporation

Sources & evidence

ORD record
ord-60e9d1c7f8614576a02163f47a82087c
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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