Sodium Hydroxide → 2-[(Cyclopentylmethyl)(ethyl)amino]-6-ethylnicotinaldehyde

HRID 906332ノート

反応式

HRID 906332 の反応式
[CH:1]1([CH2:6][N:7]([CH2:18][CH3:19])[C:8]2[C:13]([C:14]#N)=[CH:12][CH:11]=[C:10]([CH2:16][CH3:17])[N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C.[OH-:30].[Na+]>ClCCl>[CH:1]1([CH2:6][N:7]([CH2:18][CH3:19])[C:8]2[N:9]=[C:10]([CH2:16][CH3:17])[CH:11]=[CH:12][C:13]=2[CH:14]=[O:30])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 21225700Diisobutylaluminumhydride2 回HCID 673913322-[(Cyclopentylmethyl)(ethyl)amino]-6-ethylpyridine-3-carbonitrile

生成物 1

HCID 866284322-[(Cyclopentylmethyl)(ethyl)amino]-6-ethylnicotinaldehyde収率 48%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 2-[(cyclopentylmethyl)(ethyl)amino]-6-ethylpyridine-3-carbonitrile (484 mg, 1.87 mmol) in dichloromethane (5 mL) was added with diisobutylaluminum hydride (0.99 M solution in toluene, 1.99 mL, 1.97 mmol) at −78° C., and the mixture was stirred at the same temperature for 4 hours. The mixture was further added with diisobutylaluminum hydride (0.99 M solution in toluene, 0.2 mL, 0.198 mmol) at the same temperature, and the mixture was stirred at the same temperature for 45 minutes. Then, the mixture was added with 2 M aqueous sodium hydroxide, stirred at room temperature for 30 minutes, and extracted with chloroform. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to obtain 2-[(cyclopentylmethyl)(ethyl)amino]-6-ethylnicotinaldehyde (233 mg, 48%) as yellow oil.

後処理

  1. stirringthe mixture was stirred at the same temperature for 45 minutes
  2. stirringstirred at room temperature for 30 minutes
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1)

出典と根拠

ORDレコード
ord-a0a1fb7b69994a9cb939575a14430774
出典データセット
uspto-grants-2011_09
特許番号
US08012989B2

反応ノート

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