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

HRID 1508994ノート

反応式

HRID 1508994 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-26239ae189e14d3eb86160e925eadca7
出典データセット
uspto-grants-2015_12
特許番号
US09221843B2

反応ノート

読み込み中…