Hydrochloric Acid → tert-Butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylate

HRID 1465469ノート

反応式

HRID 1465469 の反応式
[C:1]([C:3]1[N:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#N.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl.C(=O)([O-])[O-:41].[Na+].[Na+]>ClCCl>[CH:1]([C:3]1[N:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)=[O:41]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 67030211Tert-butyl 4-(6-cyanopyridin-3-yl)piperazine-1-carboxylateHCID 86583787Diisobutylaluminumhydride toluene

生成物 1

HCID 58181229tert-Butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylate収率 50.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

To a solution of tert-butyl 4-(6-cyanopyridin-3-yl)piperazine-1-carboxylate (144.2 mg, 0.500 mmol) in anhydrous dichloromethane (5 ml) was added dropwise at −78° C. 1.5M diisobutylaluminum hydride toluene solution (0.4 ml, 0.6 mmol) over 5 mins. After stirring at −78° C. for 1.5 hrs, 1M hydrochloric acid (1 ml) was added. The mixture was heated to room temperature and stirred for 1 hr. Saturated aqueous sodium carbonate solution was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:3) to give tert-butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylate (73.4 mg, yield 50.4%) as a slightly yellow solid.

後処理

  1. temperatureThe mixture was heated to room temperature
  2. stirringstirred for 1 hr
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:3)

出典と根拠

ORDレコード
ord-86b9c61b91554a86af3c91140af16bee
出典データセット
uspto-grants-2015_04
特許番号
US08999989B2

反応ノート

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