Azetidine → [5-(2-(Azetidin-1-yl)ethyl)-1-methyl-1h-[1,2,3]triazol-4-yl]methanol

HRID 2183510ノート

反応式

HRID 2183510 の反応式
CS(O[CH2:6][CH2:7][C:8]1[N:12]([CH3:13])[N:11]=[N:10][C:9]=1[CH2:14][O:15][Si](C(C)(C)C)(C)C)(=O)=O.[NH:23]1[CH2:26][CH2:25][CH2:24]1>C1COCC1>[N:23]1([CH2:6][CH2:7][C:8]2[N:12]([CH3:13])[N:11]=[N:10][C:9]=2[CH2:14][OH:15])[CH2:26][CH2:25][CH2:24]1

参加物

4

反応物 2

HCID 10422AzetidineHCID 879982852-[4-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-methyl-1h-1,2,3-triazol-5-yl]ethyl methanesulphonate

生成物 1

HCID 22473219[5-(2-(Azetidin-1-yl)ethyl)-1-methyl-1h-[1,2,3]triazol-4-yl]methanol収率 29%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 2-[4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-methyl-1H-1,2,3-triazol-5-yl]ethyl methanesulphonate (642 mg, 1.84 mmol) and azetidine (2.48 ml, 18.4 mmol) in THF (10 ml) was heated at reflux for 4 h and then concentrated under reduced pressure while dry loading onto silica. The mixture was purified by column chromatography on silica using 2% MeOH/CH2Cl2 containing 1% NH3 solution as eluent. After concentrating under reduced pressure, THF (3 ml), H2O (3ml) and AcOH (9 ml) were added and the mixture stirred at RT for 60 h. The solvents were removed under reduced pressure while azeotroping with toluene (2×25 ml). The residue was dissolved in CH2Cl2, dry loaded onto silica and purified by column chromatography on silica using 15% MeOH/CH2Cl2 containing 1% NH3 solution as eluent to yield the desired hydroxymethyltriazole (103 mg, 29%). 1H NMR (360 MHz, CDCl3) δ 4.65 (2H, s), 3.94 (3H, s), 3.25 (4H, t, J=7.2 Hz), 2.76-2.62 (4H, m), 2.11 (2H, quintet, 7.2 Hz). m/z (ES+) 196 (M+H+).

後処理

  1. temperatureat reflux for 4 h
  2. concentrationconcentrated under reduced pressure
  3. customwhile dry loading onto silica
  4. customThe mixture was purified by column chromatography on silica using 2% MeOH/CH2Cl2 containing 1% NH3 solution as eluent
  5. concentrationAfter concentrating under reduced pressure, THF (3 ml), H2O (3ml) and AcOH (9 ml)
  6. additionwere added
  7. customThe solvents were removed under reduced pressure
  8. customwhile azeotroping with toluene (2×25 ml)
  9. dissolutionThe residue was dissolved in CH2Cl2
  10. customdry loaded onto silica
  11. custompurified by column chromatography on silica using 15% MeOH/CH2Cl2 containing 1% NH3 solution as eluent

出典と根拠

ORDレコード
ord-9f2836710fd6426a8fc57f24c34590d7
出典データセット
uspto-grants-2005_05
特許番号
US06900209B2

反応ノート

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