Tetrahydrofuran → 1-(1-(4-Cyanobenzyl)imidazole-5-ylmethyl)-4-(tert-butyloxycarbonyl)-(trans)2,5-dimethylpiperazine

HRID 277777ノート

反応式

HRID 277777 の反応式
[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH:13]=O)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].[CH3:17][C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([CH3:31])[CH2:20][NH:19]1.O1CCCC1.C([BH3-])#N.[Na+]>CO.O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(O)C>[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13][N:19]3[CH2:20][C@@H:21]([CH3:31])[N:22]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:23][C@@H:18]3[CH3:17])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2]

参加物

8

反応物 4

HCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrileHCID 24903576(2R,5S)-2,5-Dimethyl-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 701531721-(1-(4-Cyanobenzyl)imidazole-5-ylmethyl)-4-(tert-butyloxycarbonyl)-(trans)2,5-dimethylpiperazine

試薬・触媒・溶媒 3

HCID 11026Titanium isopropoxide触媒HCID 702Ethanol溶媒HCID 22242641Methanol--water (1/1)溶媒

反応条件

温度
60 °C

実験手順

To a round bottom flask were added 1-(4-cyanobenzyl)-5-formylimidazole (250.0 mg, 1.2 mmole) along with titanium(IV)isopropoxide (1.0 ml, 3.65 mmol), (trans) 2,5-Dimethyl-4-tertbutyloxycarbonylpiprizine (253.7 mg, 1.2 mmol) (prepared as described in Step 1), and tetrahydrofuran (0.4 ml). The reaction was heated at 60° C. for 1.25 hour. The reaction was cooled and sodiumcyanoborohydride (95.0 mg, 1.5 mmol) was added along with ethanol (0.5 ml) and the reaction was stirred at RT for 18 hours. The reaction was diluted with methanol/water (3 ml/1 ml) and the mixture filtered through celite. The filtrate was then concentrated to an oil, dissolved into methanol and put through a High Pressure Liquid Chromatography column. The desired fractions were collected, concentrated, and lyophilized to give the ditrifluoroacetic acid salt of the title compound.

後処理

  1. temperatureThe reaction was cooled
  2. filtrationthe mixture filtered through celite
  3. concentrationThe filtrate was then concentrated to an oil
  4. dissolutiondissolved into methanol
  5. customThe desired fractions were collected
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-746d9af315ab4fb7a69c9a5a5da08560
出典データセット
uspto-grants-2002_03
特許番号
US06358956B1

反応ノート

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