Ethyl 2-(5-((tert-butoxycarbonyl)amino)pyridin-2-yl)acetate → Ethyl {cis-5-[(tert-butoxycarbonyl)amino]piperidin-2-yl}acetate

HRID 602445노트

반응식

HRID 602445 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.C(O)(=O)C.[Pt]=O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][NH:13][C@@H:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 1

HCID 59224181Ethyl 2-(5-((tert-butoxycarbonyl)amino)pyridin-2-yl)acetate

생성물 1

HCID 86624143Ethyl {cis-5-[(tert-butoxycarbonyl)amino]piperidin-2-yl}acetate수율 65%

시약·촉매·용매 3

HCID 82844Platinum oxide (PtO)촉매HCID 176Acetic Acid용매HCID 702Ethanol용매

실험 절차

The mixture of ethyl {5-[(tert-butoxycarbonyl)amino]pyridin-2-yl}acetate (3.72 g, 15.6 mmol, step 4 of Example 1) and platinum oxide (300 mg) in ethanol (6 mL) and acetic acid (6 mL) was stirred under hydrogen (4 atom) at room temperature for 8 h. The mixture was filtered through a pad of Celite washing with ethanol and the filtrate was concentrated. The resulting residue was diluted with 2N aqueous sodium hydroxide solution (100 mL), and extracted with dichloromethane (100 mL×3). The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with dichloromethane/methanol (20:1) to give 2.48 g (65%) of the title compound as a colorless oil. (trans isomer 559 mg, 15% yield)

후처리

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashing with ethanol
  3. concentrationthe filtrate was concentrated
  4. additionThe resulting residue was diluted with 2N aqueous sodium hydroxide solution (100 mL)
  5. extractionextracted with dichloromethane (100 mL×3)
  6. dry with materialThe combined organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was chromatographed on a column of silica gel eluting with dichloromethane/methanol (20:1)

출처 및 근거

ORD 기록
ord-2a30f998b1d34ba495186161ff7fc25b
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906532B2

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