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

HRID 2071000노트

반응식

HRID 2071000 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 27377185-(Aminomethyl)-2-(trifluoromethyl)pyridine수율 92.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d0c3bc7110394d1fbdef21b4247913b9
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

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