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Triethylamine → (S)-3-methanesulfonyloxy-1-(4-methoxyphenethyl)pyrrolidine

HRID 1859446
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HRID 1859446 반응식
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH2:3]1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl.O>[CH3:24][S:25]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[CH2:3]1)(=[O:27])=[O:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12148702(S)-3-hydroxy-1-(4-methoxyphenethyl)pyrrolidine

생성물 1

HCID 12148703(S)-3-methanesulfonyloxy-1-(4-methoxyphenethyl)pyrrolidine

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매
2회

실험 절차

(S)-3-Hydroxy-1-(4-methoxyphenethyl)pyrrolidine (541 mg, 2.45 mmol) was dissolved in dichloromethane (15 ml). Triethylamine (272 mg, 2.69 mmol) and methanesulfonyl chloride (295 mg, 2.58 mmol) were added to the obtained solution under stirring under cooling on ice. They were stirred at 0° C. for 1 hour. The reaction liquid was distributed in dichloromethane and water. The organic layer was dried, and the solvent was evaporated under reduce pressure. The obtained residue was subjected to silica gel column chromatography. The product was eluted with dichloromethane and then with a solvent mixture of dichloromethane and methanol (50:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (S)-3-methanesulfonyloxy-1-(4-methoxyphenethyl)pyrrolidine in the form of a white solid (734 mg, 100%).

후처리

  1. temperatureunder cooling on ice
  2. stirringThey were stirred at 0° C. for 1 hour
  3. customThe reaction liquid
  4. customThe organic layer was dried
  5. customthe solvent was evaporated
  6. washThe product was eluted with dichloromethane
  7. additionwith a solvent mixture of dichloromethane and methanol (50:1)
  8. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-54bc0494b11a41cdafa7cdddfbc33338
출처 데이터셋
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06528504B2

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