Hydrochloric Acid → (2-Azetidin-2-yl-5-chlorophenyl)methanol hydrochloride

HRID 1058259노트

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HRID 1058259 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[NH:17][C:16](=O)[CH2:15]2)=[C:10]([CH2:19][O:20][Si](C(C)C)(C(C)C)C(C)C)[CH:9]=1.Cl>CCOCC>[ClH:7].[NH:17]1[CH2:16][CH2:15][CH:14]1[C:11]1[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][C:10]=1[CH2:19][OH:20]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 186723524-(4-Chloro-2-{[(triisopropylsilyl)oxy]methyl}phenyl)azetidin-2-oneHCID 21226445Aluminium lithium hydride

생성물 1

HCID 69939797(2-Azetidin-2-yl-5-chlorophenyl)methanol hydrochloride수율 200%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
0 °C

실험 절차

LAH (1 M solution in ether, 7.74 mL) was added to a stirred solution of 4-(4-chloro-2-{[(triisopropylsilyl)oxy]methyl}phenyl)azetidin-2-one (0.7122 g, 1.935 mmol) in ether (2 mL) at 0° C. The solution was heated to reflux and after 2 h was cooled to 0° C. and quenched with water (0.294 mL), 15% sodium hydroxide solution (0.294 mL) and water (0.881 mL). The mixture was sonicated to give a uniform precipitate, filtered and evaporated in vacuo to an oil. The oil was dissolved in ethanol (10 mL) and concentrated HCl (0.167 mL, 2 mmol) was added with stirring at 0° C. The reaction was warmed to ambient temperature and after 30 min was evaporated in vacuo, azeotroping with ethanol to give (2-azetidin-2-yl-5-chlorophenyl)methanol hydrochloride (0.453 g) as a crystalline solid: 1H NMR (CD3OD, 400 MHz) δ 2.79 (m, 1H), 3.14 (m, 1H), 3.87 (dt, J=4.5 and 10.0 Hz, 1H, 4.18 (q, J=9.3 Hz, 1H), 4.61 (d, J=13.1 Hz, 1H), 4.68 (d, J=13.1 Hz, 1H), 5.93 (t, J=9.0 Hz, 1H), 7.49 (m, 2H), 7.69 (d, J=8.2 Hz, 1H).

후처리

  1. temperatureThe solution was heated
  2. temperatureto reflux and after 2 h
  3. customquenched with water (0.294 mL), 15% sodium hydroxide solution (0.294 mL) and water (0.881 mL)
  4. customThe mixture was sonicated
  5. customto give a uniform precipitate
  6. filtrationfiltered
  7. customevaporated in vacuo to an oil
  8. dissolutionThe oil was dissolved in ethanol (10 mL)
  9. temperatureThe reaction was warmed to ambient temperature and after 30 min
  10. customwas evaporated in vacuo
  11. customazeotroping with ethanol

출처 및 근거

ORD 기록
ord-47a147ee26ad4c688da0995dece03ba1
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06515011B2

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