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

HRID 1805132ノート

反応式

HRID 1805132 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 108458381-(2-(tert-butyl)phenyl)pyrrolidine収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)).

後処理

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

出典と根拠

ORDレコード
ord-504810fed29a4b579cafc9e9428d34a0
出典データセット
uspto-grants-2013_01
特許番号
US08354427B2

反応ノート

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