Potassium Carbonate → 1-(6-Nitro-pyridin-3-yl)-azetidin-3-ol

HRID 593127노트

반응식

HRID 593127 반응식
F[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl.[NH:18]1[CH2:21][CH:20]([OH:22])[CH2:19]1>C(#N)C>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:18]2[CH2:21][CH:20]([OH:22])[CH2:19]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 27592903-Hydroxyazetidine hydrochlorideHCID 167481095-Fluoro-2-nitropyridine

생성물 1

HCID 592909581-(6-Nitro-pyridin-3-yl)-azetidin-3-ol수율 73%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
60 °C

실험 절차

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with acetonitrile (50 mL), 5-fluoro-2-nitropyridine (1.2 g, 7.9 mmol), K2CO3 (2.1 g, 15.8 mmol), and azetidin-3-ol hydrochloride (1.3 g, 11.9 mmol). The mixture was heated at 60° C. for 1 h. After this time the reaction was cooled to room temperature. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (50:1 to 20:1) to afford 314a (1.1 g, 73%) as a yellow solid. MS-ESI: [M+H]+ 196.0.

후처리

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. temperatureAfter this time the reaction was cooled to room temperature
  3. filtrationIt was then filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography
  6. washeluting with dichloromethane/methanol (50:1 to 20:1)

출처 및 근거

ORD 기록
ord-684570fb0ab74b21ad1bcc986aaf38ed
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238655B2

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