Borane;tetrahydrofuran → 3-Aminomethyl-6-(tert-butylthio)methyl-pyridine

HRID 1190968노트

반응식

HRID 1190968 반응식
[C:1]([S:5][CH2:6][C:7]1[N:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[NH2:14][CH2:13][C:10]1[CH:11]=[N:12][C:7]([CH2:6][S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:8][CH:9]=1

참가 물질

4

반응물 2

HCID 2723981Borane;tetrahydrofuranHCID 584955036-(Tert-butylthio)methyl-pyridine-3-carbonitrile

생성물 1

HCID 584954543-Aminomethyl-6-(tert-butylthio)methyl-pyridine수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Dissolve 6-(tert-butylthio)methyl-pyridine-3-carbonitrile (4.9 g, 23.8 mmol) in anhydrous THF (20 mL) under nitrogen and cool the mixture at 0° C. Add borane-THF complex (71.3 mL, 71.3 mmol, 1M solution in THF). Stir the reaction mixture at room temperature overnight. Pour slowly the reaction mixture into ice-cold 2N aqueous HCl (200 mL) and stir the resulting solution for 4 h. Concentrate in vacuo, take up the resulting solid with a minimum amount of methanol and filter through SCX-2 column eluting with methanol followed by 3N ammonia in methanol to obtain the title compound as a yellow oil (3.8 g, 77%). MS (ES+) m/z: 211 (M+H)+.

후처리

  1. stirringstir the resulting solution for 4 h
  2. concentrationConcentrate in vacuo
  3. filtrationfilter through SCX-2 column
  4. washeluting with methanol

출처 및 근거

ORD 기록
ord-328a67a8a12d41dc92592be214d64b13
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680091B2

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