Borane;tetrahydrofuran → 3-Aminomethyl-6-(iso-propoxy)methyl-pyridine

HRID 1190974ノート

反応式

HRID 1190974 の反応式
B.C1COCC1.[CH:7]([O:10][CH2:11][C:12]1[N:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=1)([CH3:9])[CH3:8]>Cl>[NH2:19][CH2:18][C:15]1[CH:16]=[N:17][C:12]([CH2:11][O:10][CH:7]([CH3:9])[CH3:8])=[CH:13][CH:14]=1

参加物

4

反応物 2

HCID 2723981Borane;tetrahydrofuranHCID 584956066-(Iso-propoxy)methyl-pyridine-3-carbonitrile

生成物 1

HCID 584955003-Aminomethyl-6-(iso-propoxy)methyl-pyridine収率 46.4%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

Add a solution of borane-THF complex (4.5 mL, 4.54 mmol, 1M solution in THF) to neat 6-(iso-propoxy)methyl-pyridine-3-carbonitrile (0.4 g, 2.27 mmol) and stir the mixture for 16 h at reflux. Cool to room temperature and stir for 48 h. Add 2N aqueous HCl (10 mL) until gas evolution stops and then concentrate in vacuo. Dissolve the crude mixture in methanol and filter through a SCX-2 column eluting with methanol followed by 3N ammonia in methanol to obtain the title compound (190 mg, 46%).

後処理

  1. temperatureat reflux
  2. stirringstir for 48 h
  3. concentrationconcentrate in vacuo
  4. dissolutionDissolve the crude mixture in methanol
  5. filtrationfilter through a SCX-2 column
  6. washeluting with methanol

出典と根拠

ORDレコード
ord-cdbb2bbeef9b4678b88ab5310ebb326e
出典データセット
uspto-grants-2014_03
特許番号
US08680091B2

反応ノート

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