Triethylamine → (S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine

HRID 383396

Reaction equation

HRID 383396 reaction equation
S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH3:12][C@H:13]1[CH2:17][CH2:16][CH2:15][NH:14]1.F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([C:28]([F:31])([F:30])[F:29])[CH:20]=1.C(N(CC)CC)C>C(#N)C>[CH3:12][C@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([C:28]([F:29])([F:31])[F:30])[CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2230945-Fluoro-2-nitrobenzotrifluorideHCID 44118660(S)-2-Methylpyrrolidine 4-methylbenzenesulfonate

Product 1

HCID 59395009(S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidineYield 100.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
82 °C

Procedure

To a solution of (S)-2-methylpyrrolidine tosylate (10.6 g, 41.2 mmol) in acetonitrile (85 mL) was added 4-fluoro-1-nitro-2-(trifluoromethyl)benzene (6.6 g, 31.7 mmol) dropwise and followed by triethylamine (11.0 mL, 79.3 mmol) dropwise. The reaction was heated at 82° C. for 16 h. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with 1N HCl, then dried over Na2SO4 and concentrated in vacuo to yield (S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine (8.7 g, quantitative yield). LC/MS m/z 275.3 [M+H]+.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 1N HCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5026c783114c4fe5bc0d8d53c1c77604
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Linked notes

Loading…