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

HRID 1278049

반응식

HRID 1278049 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ff8ee05668204511982e503563675df6
출처 데이터셋
uspto-grants-1981_07
특허 번호
US04279918

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