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Sodium Hydroxide → 1-[5-(Tert-butyldimethylsilanyloxymethyl)pyridin-2-yl]cyclopropylamine

HRID 589924
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HRID 589924 반응식
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]#[N:17])=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:18]([Mg]Br)[CH3:19].[OH-].[Na+]>O1CCCC1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2([NH2:17])[CH2:19][CH2:18]2)=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
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참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 542127655-(Tert-butyldimethylsilanyloxymethyl)-pyridine-2-carbonitrileHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 594069831-[5-(Tert-butyldimethylsilanyloxymethyl)pyridin-2-yl]cyclopropylamine

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매
HCID 8028
Tetrahydrofuran
용매
3회

실험 절차

5-(tert-Butyldimethylsilanyloxymethyl)-pyridine-2-carbonitrile was dissolved in tetrahydrofuran (10 ml), titanium tetraisopropoxide (0.62 ml) was added thereto, and a solution of ethylmagnesium bromide in tetrahydrofuran (1 mol/l, 4.83 ml) was added dropwise. The mixture was stirred for 1 hr 30 min. To the reaction mixture was added 1N aqueous sodium hydroxide solution (6 ml) and tetrahydrofuran (20 ml) was further added, and the mixture was stirred and filtered. The filtrate was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size 2 L, elution solvent: hexane/ethyl acetate) to give the title compound (192 mg).

후처리

  1. additionwas further added
  2. stirringthe mixture was stirred
  3. filtrationfiltered
  4. washThe filtrate was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size 2 L, elution solvent: hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-8639f9c40e36439ba7e0a8f71b202adf
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09233969B2

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