tert-Butyl 2-formyl-1H-pyrrole-1-carboxylate → [N-(dimethylethoxycarbonyl)pyrrol-2-yl](3-aminophenyl)methanol

HRID 2213663ノート

反応式

HRID 2213663 の反応式
[CH3:1][C:2]([CH3:14])([O:4][C:5]([N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH:12]=[O:13])=[O:6])[CH3:3].C[Si]([N:19]([Si](C)(C)C)[C:20]1[CH:21]=[C:22]([Mg]Cl)[CH:23]=[CH:24][CH:25]=1)(C)C>C1COCC1>[CH3:3][C:2]([CH3:14])([O:4][C:5]([N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH:12]([C:24]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:19])[CH:25]=1)[OH:13])=[O:6])[CH3:1]

参加物

4

反応物 2

HCID 5057005tert-Butyl 2-formyl-1H-pyrrole-1-carboxylateHCID 178504299HCID 178504299、化合物

生成物 1

HCID 21957618[N-(dimethylethoxycarbonyl)pyrrol-2-yl](3-aminophenyl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of N-(dimethylethoxycarbonyl)pyrrole-2-carboxaldehyde (10 g, 50 mmol) in THF (500 mL) at −30° C. under nitrogen was added dropwise to 3-[bis(trimethylsilyl)amino]phenylmagnesium chloride (55 mL of a 1M solution in THF, 55 mmol). After addition the reaction mixture was gradually warmed up and stirred at 0° C. for 1 hour, then at ambient temperature for 15 minutes. The reaction mixture was poured into ice water, and stirred for 30 minutes. The reaction mixture was extracted with ethyl ether (1 L). The combined organic layers were dried (Na2SO4) and concentrated. Chromatography on SiO2 (700 g) using 1:1 hexane/ethyl acetate afforded [N-(dimethylethoxycarbonyl)pyrrol-2-yl](3-aminophenyl)methanol (11.2 g).

後処理

  1. additionAfter addition the reaction mixture
  2. temperaturewas gradually warmed up and
  3. waitat ambient temperature for 15 minutes
  4. stirringstirred for 30 minutes
  5. extractionThe reaction mixture was extracted with ethyl ether (1 L)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-4522992528e14ea8babc3e79fad1260f
出典データセット
uspto-grants-2006_09
特許番号
US07105563B2

反応ノート

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