Triethylamine → (R)-N,N-Dimethyl-1-(4-nitro-2-(trifluoromethyl)benzyl)pyrrolidin-3-amine

HRID 923217Notes

Reaction equation

HRID 923217 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].CCN(CC)CC.[CH3:23][N:24]([CH3:30])[C@@H:25]1[CH2:29][CH2:28][NH:27][CH2:26]1>C(Cl)Cl>[CH3:23][N:24]([CH3:30])[C@@H:25]1[CH2:29][CH2:28][N:27]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=2[C:12]([F:15])([F:14])[F:13])[CH2:26]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 468387611-(Bromomethyl)-4-nitro-2-(trifluoromethyl)benzene

Product 1

HCID 66735770(R)-N,N-Dimethyl-1-(4-nitro-2-(trifluoromethyl)benzyl)pyrrolidin-3-amineYield 60.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 1-(bromomethyl)-4-nitro-2-(trifluoromethyl)benzene (17.5 mmol, 75% pure) in 40 mL of DCM was added Et3N (2.69 mL, 19.3 mmol) and (R)-(+)-3-(dimethylamino)pyrrolidine (2.0 g, 17.5 mmol). After stirring overnight at ambient temperature under an atmosphere of N2, the reaction solution was concentrated, added aq. NaHCO3 (100 mL), and the resulting mixture extracted with DCM (4×50 mL). The combined organic layer was dried over Na2SO4, filtered, concentrated, and the resulting residue was purified by silica gel chromatography (eluted with 0-10% MeOH/DCM) to provide 3.35 g of product as a yellow oil.

Workup

  1. concentrationthe reaction solution was concentrated
  2. additionadded aq. NaHCO3 (100 mL)
  3. extractionthe resulting mixture extracted with DCM (4×50 mL)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe resulting residue was purified by silica gel chromatography (eluted with 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-5b438a61a2484d73b33ab77edc01db6a
Source dataset
uspto-grants-2016_03
Patent number
US09278971B2

Reaction notes

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