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

HRID 1508995노트

반응식

HRID 1508995 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-79be5676ea8d42ba819c1d2d3af0385b
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221843B2

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