2-Chloro-5-nitropyridine → Methyl [1-(5-nitropyridin-2-yl)piperidin-4-yl]acetate

HRID 557690노트

반응식

HRID 557690 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][O:12][C:13](=[O:21])[CH2:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH3:11][O:12][C:13](=[O:21])[CH2:14][CH:15]1[CH2:16][CH2:17][N:18]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:19][CH2:20]1

참가 물질

5

반응물 3

HCID 783082-Chloro-5-nitropyridineHCID 81531DiisopropylethylamineHCID 1515259Methyl 4-piperidineacetate

생성물 1

HCID 47357980Methyl [1-(5-nitropyridin-2-yl)piperidin-4-yl]acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
120 °C

실험 절차

To a mixture of 2-chloro-5-nitropyridine (476 mg, 3.0 mmol) and 4-piperidine acetic acid methyl ester (471 mg, 3.0 mmol) in tetrahydrofuran (10 mL) was added diisopropylethylamine (1.0 mL, 5.74 mmol). The mixture was heated in a microwave at 120° C. for 30 minutes. The mixture was evaporated to dryness and extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate and solvents were evaporated. The residue was purified using flash chromatography (eluting with ethyl acetate and hexanes) to give (5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid methyl ester as a yellow solid. The NMR spectrum obtained on the sample is compatible with its structure.

후처리

  1. customThe mixture was evaporated to dryness
  2. extractionextracted with ethyl acetate and water
  3. dry with materialThe organic layer was dried over sodium sulfate and solvents
  4. customwere evaporated
  5. customThe residue was purified
  6. washflash chromatography (eluting with ethyl acetate and hexanes)

출처 및 근거

ORD 기록
ord-98992c37d85049a59a2a8afabfff37b4
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058299B2

반응 노트

불러오는 중…