Triethylamine → HCID 68410552, compound

HRID 404599Notes

Reaction equation

HRID 404599 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.F[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([C:17]([F:20])([F:19])[F:18])[CH:9]=1.CCN(CC)CC>C(#N)C>[CH3:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([C:17]([F:18])([F:20])[F:19])[CH:9]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2230945-Fluoro-2-nitrobenzotrifluorideHCID 11029760(R)-3-METHYLPYRROLIDINE

Product 1

HCID 68410552HCID 68410552, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (R)-3-methylpyrrolidine (1.000 g, 8.226 mmol), 4-fluoro-1-nitro-2-(trifluoromethyl)benzene (1.72 g, 8.226 mmol) and Et3N (2.080 g, 2.865 mL, 20.56 mmol) in ACN was heated at 80° C. for 5 hours. The reaction was cooled to RT, quenched with water, the layers separated and the aqueous layer was extracted with DCM. The combined organic layer was washed with 1M HCl to remove the unreacted amine. The organic layer was dried over Na2SO4, filtered and concentrated to give (S)-3-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine (1.97 g, 7.184 mmol) MS 275.0 m/z (MH+).

Workup

  1. customquenched with water
  2. customthe layers separated
  3. extractionthe aqueous layer was extracted with DCM
  4. washThe combined organic layer was washed with 1M HCl
  5. customto remove the unreacted amine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-931096984a9d4650bc76dfbd27fd69d0
Source dataset
uspto-grants-2014_06
Patent number
US08748612B2

Reaction notes

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