Methyl 4-(4-oxobut-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate → 4-(1-(tert-Butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoic acid

HRID 8746

반응식

HRID 8746 반응식
[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][C:6]1([C:19]([O:21][CH3:22])=[O:20])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.CC(C)=[O:25].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:15]([O:14][C:12]([N:9]1[CH2:8][CH2:7][C:6]([CH2:5][CH2:4][CH2:3][C:2]([OH:25])=[O:1])([C:19]([O:21][CH3:22])=[O:20])[CH2:11][CH2:10]1)=[O:13])([CH3:17])([CH3:18])[CH3:16]

참가 물질

4

반응물 2

HCID 86597419Methyl 4-(4-oxobut-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylateHCID 131709961Jones' reagent

생성물 1

HCID 219839874-(1-(tert-Butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoic acid

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of methyl 4-(4-oxobut-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate (23.0 g, 0.0734 mol) from Step C in acetone (775 mL) at room temperature was added Jones reagent (28.2 mL, 2.6M) via syringe. After 5 min, the reaction mixture was concentrated. The residue was taken up in water and diethyl ether and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound (23.4 g) which was used in the next step without further purification.

후처리

  1. concentrationthe reaction mixture was concentrated
  2. extractiondiethyl ether and extracted three times with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-190dcd50c65c412eb9c6458f3623a7b2
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091211B2

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