Sodium Carbonate → (2R, 4R)-(+)-2-(ethoxycarbonyl)-4-hydroxy-1-(4-methoxy phenethyl) pyrrolidine

HRID 2304402노트

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HRID 2304402 반응식
Cl.[CH2:2]([O:4][C:5]([C@H:7]1[CH2:11][C@@H:10]([OH:12])[CH2:9][NH:8]1)=[O:6])[CH3:3].C(=O)([O-])[O-].[Na+].[Na+].[CH3:19][O:20][C:21]1[CH:29]=[CH:28][C:24]([CH2:25][CH2:26]Br)=[CH:23][CH:22]=1>C(#N)C.[I-].[Na+]>[CH2:2]([O:4][C:5]([C@H:7]1[CH2:11][C@@H:10]([OH:12])[CH2:9][N:8]1[CH2:26][CH2:25][C:24]1[CH:28]=[CH:29][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1)=[O:6])[CH3:3]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 12709308Ethyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

생성물 1

HCID 57269395(2R, 4R)-(+)-2-(ethoxycarbonyl)-4-hydroxy-1-(4-methoxy phenethyl) pyrrolidine수율 59.2%

시약·촉매·용매 2

HCID 5238Sodium Iodide촉매HCID 6342Acetonitrile용매

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온도
42.5 °C

실험 절차

To a suspension of 6.60 g (33.7 mmol) of (2R, 4R)-(+)-2-(ethoxycarbonyl)-4-hydroxypyrrolidine hydrochloride in acetonitrile (60 ml) were added 8.22 g (77.6 mmol) of sodium carbonate, 4-methoxyphenethyl bromide (8.71 g, 40.5 mmol), and sodium iodide (150mg, 1.0 mmol) and the mixture was stirred at 40-45° C. for 65 h. The mixture was concentrated in vacuo and water was added to the residue, and the products were extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride and the products were extracted with 10% aqueous hydrochloride. The extract was washed with ethyl acetate, basified with potassium carbonate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain oily (2R, 4R)-(+)-2-(ethoxycarbonyl)-4-hydroxy-1-(4-methoxy phenethyl) pyrrolidine (5.85 g, 59.1%).

후처리

  1. concentrationThe mixture was concentrated in vacuo and water
  2. additionwas added to the residue
  3. extractionthe products were extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium chloride
  5. extractionthe products were extracted with 10% aqueous hydrochloride
  6. washThe extract was washed with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with saturated aqueous sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6ccdb738df6b4affb83b91edc14ec7be
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06436922B1

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