Triethylamine → HCID 68328080、化合物

HRID 2281244ノート

反応式

HRID 2281244 の反応式
Cl[C:2](Cl)([O:4][C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[Br:13][C:14]1[CH:15]=[C:16]([CH2:20][NH2:21])[CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C.[N:29]12[CH2:36]C[CH:32]([CH2:33][CH2:34]1)[CH:31](O)[CH2:30]2>C1COCC1>[Br:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[CH2:20][NH:21][C:5](=[O:11])[O:4][CH:2]1[CH:32]2[CH2:33][CH2:34][N:29]([CH2:30][CH2:31]2)[CH2:36]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 15381(+-)-3-QuinuclidinolHCID 94429TriphosgeneHCID 457587Benzenemethanamine, 3-bromo-

生成物 1

HCID 68328080HCID 68328080、化合物収率 74.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred and cooled (0° C.) solution of triphosgene (0.80 g, 2.7 mmol) in THF (20 mL) was added, dropwise, a mixture of (3-bromophenyl)methanamine (1.0 g, 5.4 mmol) and triethylamine (1.08 g, 10.7 mmol) in THF (30 mL) over 2 h. After the addition was complete, the mixture was refluxed for 1 h and then cooled to room temperature. Quinuclidin-3-ol (1.40 g, 10.7 mmol) was added, and the mixture was refluxed for 18 h. The solvent was removed in vacuo, and the residue was dissolved in EtOAc, washed with water, dried over Na2SO4, and concentrated. The crude residue was purified by silica gel column chromatography (eluting with EtOAc/methanol=10/1) to give quinuclidin-3-yl 3-bromobenzylcarbamate as a colourless liquid (0.68 g, 37%).

後処理

  1. additionwas added
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed for 1 h
  4. temperaturethe mixture was refluxed for 18 h
  5. customThe solvent was removed in vacuo
  6. dissolutionthe residue was dissolved in EtOAc
  7. washwashed with water
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe crude residue was purified by silica gel column chromatography (eluting with EtOAc/methanol=10/1)

出典と根拠

ORDレコード
ord-483e2340512c4234933785d2aaf7787e
出典データセット
uspto-grants-2015_09
特許番号
US09139580B2

反応ノート

読み込み中…