HCID 59410064, compound → HCID 59410057, compound

HRID 1915500Notes

Reaction equation

HRID 1915500 reaction equation
Br[CH2:2][C@@H:3]1[CH2:7][C:6]([F:9])([F:8])[CH2:5][N:4]1[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([C:19]([F:22])([F:21])[F:20])[CH:11]=1>C(OCC)(=O)C.[Pd]>[F:9][C:6]1([F:8])[CH2:5][N:4]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([C:19]([F:20])([F:21])[F:22])[CH:11]=2)[C@H:3]([CH3:2])[CH2:7]1

Participants

4

Reactant 1

HCID 59410064HCID 59410064, compound

Product 1

HCID 59410057HCID 59410057, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-(bromomethyl)-4,4-difluoro-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine (230 mg, 0.59 mmol) was dissolved in ethyl acetate (5 mL) and TEA (90 mg, 124 μL, 0.89 mmol) and the flask was flushed with nitrogen. 10% Pd/C (58 mg, 0.05 mmol) catalyst was added and the reaction mixture was stirred overnight under an atmosphere of hydrogen. The reaction mixture was filtered, treated with 50% saturated NaHCO3, and extracted with ethyl acetate. The organic layer was dried over Na2SO4, filtered and concentrated to provide (R)-4-(4,4-difluoro-2-methylpyrrolidin-1-yl)-2-(trifluoromethyl)aniline as a purple oil (164 mg, 99% yield). 1H NMR (400 MHz, DMSO-d6) δ 6.81 (s, 2H), 6.58 (s, 1H), 4.92 (s, 2H), 4.07-4.01 (m, 1H), 3.74-3.63 (m, 1H), 3.60-3.50 (m, 1H), 2.75-2.60 (m, 1H), 2.22-2.11 (m, 1H), 1.10 (d, J=6.2 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiontreated with 50% saturated NaHCO3
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2ce0763ddc9e4a38ad503ee6de333b72
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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