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

HRID 1805132노트

반응식

HRID 1805132 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)).

후처리

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

출처 및 근거

ORD 기록
ord-504810fed29a4b579cafc9e9428d34a0
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354427B2

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