Water → 2-(3-Methoxybenzyl)-1-methylpyrrolidine

HRID 1278049

反応式

HRID 1278049 の反応式
[Na].CN(C)[C:4]1[CH2:8][CH2:7][CH2:6][N+:5]=1[CH3:9].COS([O-])(=O)=O.C(OC(=O)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)C.O>C(O)C.C(OCC)C>[CH3:29][O:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH3:9]

参加物

7

反応物 4

HCID 962WaterHCID 2774971Ethyl 3-methoxyphenylacetateHCID 5360545SodiumHCID 1784830372-Dimethylamino-1-methyl-1-pyrrolinium methylsulfate

生成物 1

HCID 234525002-(3-Methoxybenzyl)-1-methylpyrrolidine

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒

実験手順

Add a solution of 8.1 g of sodium in 160 ml of ethanol dropwise at 90°, with stirring, in a stream of nitrogen to 83.4 g of 2-dimethylamino-1-methyl-1-pyrrolinium-methylsulfate and 48.3 g of 3-methoxyphenylacetic acid ethyl ester. Stir the resulting reaction mixture for a further 30 minutes at 90° and then distribute the reaction mixture between 300 ml of water and 300 ml of diethyl ether. Concentrate the ether phase and boil the residue with conc. hydrochloric acid until carbon dioxide ceases to evolve. After cooling, alkalize the boiled residue with 6 N sodium hydroxide solution before extracting it with diethyl ether. Dry the ether extract over sodium sulfate; concentrate it, and reduce the concentrate in methanol with platinum/hydrogen. Separate the catalyst by filtration, concentrate the filtrate and distil to obtain a yield of 23.0 g (45% of theory) of title compound (b.p. 88° at 0.005 mm of Hg).

後処理

  1. customthe resulting reaction mixture for a further 30 minutes at 90°
  2. concentrationConcentrate the ether phase
  3. temperatureAfter cooling
  4. extractionbefore extracting it with diethyl ether
  5. dry with materialDry the ether
  6. extractionextract over sodium sulfate
  7. concentrationconcentrate it
  8. concentrationconcentrate in methanol with platinum/hydrogen
  9. customSeparate the catalyst
  10. filtrationby filtration
  11. concentrationconcentrate the filtrate
  12. customdistil

出典と根拠

ORDレコード
ord-ff8ee05668204511982e503563675df6
出典データセット
uspto-grants-1981_07
特許番号
US04279918

関連ノート

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