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

HRID 1058259ノート

反応式

HRID 1058259 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-47a147ee26ad4c688da0995dece03ba1
出典データセット
uspto-grants-2003_02
特許番号
US06515011B2

反応ノート

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