(+-)-3-Quinuclidinol → Quinuclidin-3-yl2-bromophenylcarbamate

HRID 2274918ノート

反応式

HRID 2274918 の反応式
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[H-].[Na+].[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]=[C:20]=[O:21]>C1COCC1>[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][C:20](=[O:21])[O:9][CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1

参加物

5

反応物 3

HCID 15381(+-)-3-QuinuclidinolHCID 24758Sodium hydrideHCID 1370972-Bromophenyl isocyanate

生成物 1

HCID 68327765Quinuclidin-3-yl2-bromophenylcarbamate収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of quinuclidin-3-ol (382 mg, 3.00 mmol) in THF (15 mL) was added NaH [60% dispersion in mineral oil] (156 mg, 3.90 mmol) at room temperature. The mixture was stirred for 15 min and 2-bromophenyl isocyanate (594 mg, 3.00 mmol) was added under stirring. The resulting mixture was stirred at room temperature for 18 h, quenched with brine and extracted with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated. The resulting crude product was purified by silica gel column chromatography (EtOAc/methanol 3:1) to give the product quinuclidin-3-yl 2-bromophenylcarbamate as viscous oil (0.80 g, 82%).

後処理

  1. stirringunder stirring
  2. stirringThe resulting mixture was stirred at room temperature for 18 h
  3. customquenched with brine
  4. extractionextracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by silica gel column chromatography (EtOAc/methanol 3:1)

出典と根拠

ORDレコード
ord-0c32982d12da42279f7b5219d0c012fb
出典データセット
uspto-grants-2015_09
特許番号
US09126993B2

反応ノート

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