Thionyl Chloride → HCID 53985286、化合物

HRID 975820

反応式

HRID 975820 の反応式
[Br:1][CH2:2][CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([OH:7])=O.S(Cl)(Cl)=O.[CH2:18]1[CH:26]2[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]2)[CH2:20][NH:19]1.C(N(C(C)C)CC)(C)C>ClCCl.C(OCC)C.CCOC(C)=O>[CH2:18]1[CH:26]2[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]2)[CH2:20][N:19]1[C:5](=[O:7])[CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][CH2:2][Br:1]

参加物

8

反応物 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 409979OctahydroisoindoleHCID 167406054-Bromo-2-phenylbutanoic acid

生成物 1

HCID 53985286HCID 53985286、化合物

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4-Bromo-2-phenylbutanoic acid (4.86 g, 0.02 mol) and thionyl chloride (2.2 mL, 0.03 mol) were refluxed in dichloromethane (100 mL) under nitrogen for 3 hours. The solution was evaporated and flushed with benzene three times. The residue was dissolved in diethyl ether (50 mL) and cooled in an ice bath. Octahydroisoindole (2.5 g, 0.02 mol) and diisopropylethylamine (3.5 mL, 0.02 mol) dissolved in diethyl ether (50 mL) were added and the reaction was stirred for 60 hours at room temperature. TLC (Uniplate/EtOAc) showed essentially complete reaction. The solution was washed with water, sat. NaHCO3, and dried (Na2SO4). Evaporation of solvent left crude product.

後処理

  1. customThe solution was evaporated
  2. customflushed with benzene three times
  3. dissolutionThe residue was dissolved in diethyl ether (50 mL)
  4. temperaturecooled in an ice bath
  5. additionwere added
  6. customreaction
  7. washThe solution was washed with water, sat. NaHCO3
  8. dry with materialdried (Na2SO4)
  9. customEvaporation of solvent
  10. waitleft crude product

出典と根拠

ORDレコード
ord-b5e44369ca664c2f92d3bae4eb1427f9
出典データセット
uspto-grants-1997_03
特許番号
US05610154

関連ノート

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