Aluminium lithium hydride → 5-(Aminomethyl)-2-(trifluoromethyl)pyridine

HRID 2071000ノート

反応式

HRID 2071000 の反応式
[N:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][CH:10]=1)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:13][C:11]([F:12])([F:14])[C:8]1[N:9]=[CH:10][C:5]([CH2:4][NH2:1])=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 866017575-(Azidomethyl)-2-(trifluoromethyl)pyridine

生成物 1

HCID 27377185-(Aminomethyl)-2-(trifluoromethyl)pyridine収率 92.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

5-(azidomethyl)-2-(trifluoromethyl)pyridine (2.6 g, 12.86 mmol) in THF at −78° C. was added LAH (0.54 g, 14.2 mmol). The resulting mixture was stirred for 15 min. and warmed to room temperature for one hour. Then the reaction was quenched with saturated aqueous NH4Cl and stirred for a couple of hours. Anhydrous Na2SO4 was added to make the mixture clear two phases, filtered and washed with EtOAc. The combined organic solution was concentrated to provide (6-(trifluoromethyl)pyridin-3-yl)methanamine as a red syrup (2.1 g). 1H NMR (300 MHz, CDCl3+CD3OD), d: 8.729 (s, 1H), 7.928 (d, J=9.1 Hz, 1H), 7.706 (d, J=9.1 Hz, 1H), 4.054 (s, 2H).

後処理

  1. customThen the reaction was quenched with saturated aqueous NH4Cl
  2. stirringstirred for a couple of hours
  3. additionAnhydrous Na2SO4 was added
  4. filtrationfiltered
  5. washwashed with EtOAc
  6. concentrationThe combined organic solution was concentrated

出典と根拠

ORDレコード
ord-d0c3bc7110394d1fbdef21b4247913b9
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

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