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

HRID 2100665

反応式

HRID 2100665 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.CC(C[AlH]CC(C)C)C.Cl.C1C[O:35]CC1>>[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:35]

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2 回HCID 14487Diisobutylaluminum hydrideHCID 67030211Tert-butyl 4-(6-cyanopyridin-3-yl)piperazine-1-carboxylate

生成物 1

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

実験手順

To a solution of tert-butyl 4-(6-cyano-pyridin-3-yl)-piperazine-1-carboxylate (2.15 mmol) in THF (20 mL) is added a solution of DIBAL-H in THF (1.0 M, 13 mmol) dropwise and the reaction mixture is stirred at room temperature for 15 minutes. After it is cooled to 0° C., the reaction mixture is mixed with a solution of aqueous HCl (2 N, 5 mL) after which the reaction mixture is partitioned between saturated Na2CO3 solution and EtOAc. The aqueous phase is extracted with EtOAc. The combined organic extracts are washed with saturated aqueous NaCl and dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (3:7 hexanes/EtOAc) to give tert-butyl 4-(6-formyl-pyridin-3-yl)-piperazine-1-carboxylate.

後処理

  1. temperatureAfter it is cooled to 0° C.
  2. customis partitioned between saturated Na2CO3 solution and EtOAc
  3. extractionThe aqueous phase is extracted with EtOAc
  4. washThe combined organic extracts are washed with saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration
  7. customthe residue is purified by silica gel chromatography (3:7 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-07288dd9e14e47ea90d15f87eb67aeb8
出典データセット
uspto-grants-2009_08
特許番号
US07572811B2

関連ノート

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