Toluene → 1-(2-(tert-butyl)phenyl)pyrrolidine

HRID 1805132Notes

Reaction equation

HRID 1805132 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:15](=O)[CH2:14][CH2:13][C:12]1=O)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC=CC=1>C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 1140TolueneHCID 107995252,5-Pyrrolidinedione, 1-[2-(1,1-dimethylethyl)phenyl]-

Product 1

HCID 108458381-(2-(tert-butyl)phenyl)pyrrolidineYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-tert-butylphenyl)pyrrolidine-2,5-dione (500 mg, 2.16 mmol) in THF (10 mL) was added BH3 in toluene (350 mg, 1.72 mmol) dropwise and the reaction mixture was heated to reflux overnight. The reaction was cooled to room temperature and quenched with methanol (until the evolution of H2 ceased). The solvent was evaporated to obtain 1-(2-tert-butylphenyl)pyrrolidine (350 mg, 80%) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.30 (s, 1H), 7.28 (s, 1H), 7.15 (d, J=0.9 Hz, 1H), 7.07-7.01 (m, 1H), 2.90 (s, 4H), 1.88-1.78 (m, 4H), 1.35 (s, 9H). LC/MS: m/z 204.1 (M+H)+ at 0.88 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customquenched with methanol (until the evolution of H2
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-504810fed29a4b579cafc9e9428d34a0
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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