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

HRID 2100665

반응식

HRID 2100665 반응식
[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]

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2회HCID 14487Diisobutylaluminum hydrideHCID 67030211Tert-butyl 4-(6-cyanopyridin-3-yl)piperazine-1-carboxylate

생성물 1

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-07288dd9e14e47ea90d15f87eb67aeb8
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572811B2

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