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

HRID 1508995ノート

反応式

HRID 1508995 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[N+:5]([O-])=[C:4]2[CH2:13][CH2:14][CH2:15][C:3]=12.P(Cl)(Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[N:5]=[C:4]2[CH2:13][CH2:14][CH2:15][C:3]=12

参加物

4

反応物 2

HCID 24387Phosphorus trichlorideHCID 901107724-chloro-2-isopropoxy-6,7-dihydro-5H-cyclopenta[b]pyridine oxide

生成物 1

HCID 901123734-chloro-2-isopropoxy-6,7-dihydro-5H-cyclopenta[b]pyridine収率 77%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-chloro-2-isopropoxy-6,7-dihydro-5H-cyclopenta[b]pyridine 1-oxide (0.079 g, 0.35 mmol) in methylene chloride (5 mL) was added phosphorous trichloride (0.096 g, 0.70 mmol). The mixture stirred at rt for 30 min. After this time, the mixture was quenched with a saturated solution of NaHCO3 and extracted with methylene chloride. The organic layer were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.057 g, 77%) as a clear oil. MW=211.69. 1H NMR (CDCl3, 300 MHz) δ 6.47 (s, 1H), 5.27-5.18 (m, 1H), 3.01-2.84 (m, 4H), 2.11 (quin, J=7.5 Hz, 2H), 1.31 (d, J=6.0 Hz, 6H); APCI MS m/z 212 [M+H]+.

後処理

  1. customAfter this time, the mixture was quenched with a saturated solution of NaHCO3
  2. extractionextracted with methylene chloride
  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, hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-79be5676ea8d42ba819c1d2d3af0385b
出典データセット
uspto-grants-2015_12
特許番号
US09221843B2

反応ノート

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