Methanol → Methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate

HRID 2139

反応式

HRID 2139 の反応式
[C:1](Cl)(=O)C.CO.[CH2:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH:9]([C:17]([OH:19])=[O:18])[NH:8]1>CN(C=O)C>[CH3:1][O:18][C:17]([CH:9]1[CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][NH:8]1)=[O:19]

参加物

5

反応物 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 954891,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

生成物 1

HCID 4685119Methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate収率 46.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Acetyl chloride (0.88 g) was added to methanol (100 ml) with stirring at 0° C. After 10 minutes, 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (J. Am. Chem. Soc., 1962, 48, 4487-4494) (2.0 g) was added; the reaction was allowed to warm to room temperature and stirred overnight. DMF (1 ml) was then added and stirring was then continued for a further 24 h. The solvent was removed in vacuo; dichloromethane was added and the solid thus formed was filtered off and partitioned between dichloromethane (50 ml) and saturated aqueous sodium hydrogen carbonate solution (50 ml). The organic phase was dried (magnesium sulphate), filtered, and the filtrate evaporated in vacuo to yield the title compound as a pale yellow oil (1.0 g).

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. stirringstirring
  4. waitwas then continued for a further 24 h
  5. customThe solvent was removed in vacuo
  6. additiondichloromethane was added
  7. customthe solid thus formed
  8. filtrationwas filtered off
  9. custompartitioned between dichloromethane (50 ml) and saturated aqueous sodium hydrogen carbonate solution (50 ml)
  10. dry with materialThe organic phase was dried (magnesium sulphate)
  11. filtrationfiltered
  12. customthe filtrate evaporated in vacuo

出典と根拠

ORDレコード
ord-f942832a149344ee8ae24b50f8c14966
出典データセット
uspto-grants-1998_03
特許番号
US05728712

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