Isopropanol → 4-chloro-2-isopropoxy-6,7-dihydro-5H-cyclopenta[b]pyridine oxide

HRID 1508994노트

반응식

HRID 1508994 반응식
[CH:1]([OH:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].Cl[C:12]1[N+:17]([O-:18])=[C:16]2[CH2:19][CH2:20][CH2:21][C:15]2=[C:14]([Cl:22])[CH:13]=1>O1CCOCC1.C(Cl)Cl>[Cl:22][C:14]1[CH:13]=[C:12]([O:4][CH:1]([CH3:3])[CH3:2])[N+:17]([O-:18])=[C:16]2[CH2:19][CH2:20][CH2:21][C:15]=12

참가 물질

6

반응물 3

HCID 3776IsopropanolHCID 23665647Potassium tert-butoxideHCID 901125362,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine 1-oxide

생성물 1

HCID 901107724-chloro-2-isopropoxy-6,7-dihydro-5H-cyclopenta[b]pyridine oxide수율 89%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매2회

실험 절차

To a solution of iso-propanol (0.047 g, 0.79 mmol) in dioxane (3 mL) at rt was added potassium tert-butoxide (0.053 g, 0.47 mmol). The mixture was stirred at rt for 30 min. Then, 2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine 1-oxide (0.100 g, 0.39 mmol) in dioxane (1 mL) was added and the mixture was heated under microwave irradiation to 100° C. for 30 min. After this time, the mixture was diluted with methylene chloride and washed with water. The organic layer were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the title compound (0.079 g, 88%) as a white solid. MW=227.69. 1H NMR (CDCl3, 300 MHz) δ 6.73 (s, 1H), 4.90-4.85 (m, 1H), 3.23 (t, J=7.5 Hz, 2H), 3.00 (t, J=7.5 Hz, 2H), 2.20 (quin, J=7.5 Hz, 2H), 1.44 (d, J=6.0 Hz, 6H); APCI MS m/z 228 [M+H]+.

후처리

  1. temperaturethe mixture was heated under microwave irradiation to 100° C. for 30 min
  2. washwashed with water
  3. dry with materialThe organic layer were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica, dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-26239ae189e14d3eb86160e925eadca7
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221843B2

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