Imidazole → HCID 68976392、化合物

HRID 749445ノート

反応式

HRID 749445 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][NH:13][CH3:14])[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.N1C=CN=C1.[CH:20]([Si:23]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])Cl)([CH3:22])[CH3:21]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:9][CH2:10][O:11][Si:23]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:20]([CH3:22])[CH3:21])[CH2:12][NH:13][CH3:14])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 69278839HCID 69278839、化合物

生成物 1

HCID 68976392HCID 68976392、化合物収率 76.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3-(4-Bromophenyl)-4-(methylamino)butan-1-ol (see Chem. Pharm. Bull. 46, 1998, 242; 1.77 g, 6.86 mmol) was dissolved in CH2Cl2 (100 mL) at 0° C. under argon. Imidazole (1.22 g, 17.9 mmol) was added, the mixture stirred for 10 min and then triisopropylchlorosilan (3.16 g, 16.4 mmol) was added with cooling. The mixture was stirred at room temperature for 48 h and then washed twice with water (100 mL) and brine. The solvent was removed by evaporation and the residue flash chromatographed on silica gel (CH2Cl2-Methanol-NH4OH, 15:1:0.1). There was obtained 2.17 g (75%) of {2-(4-bromophenyl)-4-[(triisopropylsilyl)oxy]butyl}methylamine as an oil. 1H NMR (300 MHz, CDCl3): 0.9-1.1 (m, 21H), 1.6-1.9 (m, 2H), 2.4 (s, 3H), 2.7-2.8 (m, 2H), 3.0-3.1 (m, 1H), 3.4-3.6 (m, 2H), 7.1 (d, 2H), 7.4 (d, 2H).

後処理

  1. temperaturewith cooling
  2. stirringThe mixture was stirred at room temperature for 48 h
  3. washwashed twice with water (100 mL) and brine
  4. customThe solvent was removed by evaporation
  5. customthe residue flash chromatographed on silica gel (CH2Cl2-Methanol-NH4OH, 15:1:0.1)

出典と根拠

ORDレコード
ord-e4c72d359eaa4bfa9ae3bc40df150b3f
出典データセット
uspto-grants-2008_07
特許番号
US07402581B2

反応ノート

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