Diethylamine → 3-[3-(2-Bromobenzyl)-3H-imidazol-4-yl]-3-methylbutan-1-ol

HRID 923286ノート

反応式

HRID 923286 の反応式
[Si]([O:8][CH2:9][CH2:10][C:11]([C:14]1[N:15]=[CH:16][N:17](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:18]=1)([CH3:13])[CH3:12])(C(C)(C)C)(C)C.[Br:38][C:39]1[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=1[CH2:41]Br.C(NCC)C.Cl.O1CCOCC1.C([O-])(O)=O.[Na+]>CC#N.CO>[Br:38][C:39]1[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=1[CH2:41][N:15]1[C:14]([C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][OH:8])=[CH:18][N:17]=[CH:16]1

参加物

8

反応物 5

HCID 8021DiethylamineHCID 769652-Bromobenzyl bromideHCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 536308684-[3-(tert-butyldimethylsilanyloxy)-1,1-dimethylpropyl]-1-trityl-1H-imidazole

生成物 1

HCID 588271963-[3-(2-Bromobenzyl)-3H-imidazol-4-yl]-3-methylbutan-1-ol

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒2 回

反応条件

温度
80 °C

実験手順

To a solution of 4-[3-(tert-butyldimethylsilanyloxy)-1,1-dimethylpropyl]-1-trityl-1H-imidazole (650 mg, 1.27 mmol) in CH3CN (10 mL) at ambient temperature is added a solution of 2-bromobenzyl bromide (420 mg, 1.68 mmol) in CH3CN (10 mL). The resulting solution is stirred at 80° C. for 6 h. The mixture is cooled to ambient temperature and diethylamine (2 mL) is added, followed by MeOH (10 mL) and the mixture is heated at 75° C. for 1 hr and stirred at ambient temperature overnight. To the reaction mixture is added HCl/dioxane (4 M, 5 mL, 20 mmol) and stirred at ambient temperature for 1 h. The mixture is neutralized with saturated aqueous NaHCO3 and concentrated. The residue is partitioned between CH2Cl2 and brine. The organic layer is washed with brine, dried over Na2SO4 and concentrated to give an oil, which is subjected to flash chromatography (silica gel) eluting with MeOH:CH2Cl2 to yield the desired compound. MS (ESI) m/z 323 (M+H).

後処理

  1. temperatureThe mixture is cooled to ambient temperature
  2. temperaturethe mixture is heated at 75° C. for 1 hr
  3. stirringstirred at ambient temperature overnight
  4. stirringstirred at ambient temperature for 1 h
  5. concentrationconcentrated
  6. customThe residue is partitioned between CH2Cl2 and brine
  7. washThe organic layer is washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customto give an oil, which
  11. washeluting with MeOH

出典と根拠

ORDレコード
ord-5aa0f0cf2e134e0088c95317146d5e5c
出典データセット
uspto-grants-2016_03
特許番号
US09278969B2

反応ノート

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