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Triethylamine → (s)-3-Methanesulfonyloxy-1-[3-(4-methoxyphenyl)propyl]pyrrolidine

HRID 1859457
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HRID 1859457 반응식
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:3]1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl.O>[CH3:25][S:26]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[CH2:3]1)(=[O:28])=[O:27]
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57440106(S)-3-Hydroxy-1-[3-(4-methoxyphenyl)propyl]pyrrolidine

생성물 1

HCID 57440107(s)-3-Methanesulfonyloxy-1-[3-(4-methoxyphenyl)propyl]pyrrolidine

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane
용매
2회

실험 절차

(S)-3-Hydroxy-1-[3-(4-methoxyphenyl)propyl]pyrrolidine (310 mg, 1.32 mmol) was dissolved in dichloromethane (10 ml). Triethylamine (173 mg, 1.71 mmol) and methanesulfonyl chloride (196 mg, 1.71 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 (50:1) of dichloromethane and methanol. The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (S)-3-methanesulfonyloxy-1-[3-(4-methoxyphenyl)propyl] pyrrolidine in the form of a light yellow oil (336 mg, 81%).

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. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-91aeb210ce3f4201812a26df171bcba2
출처 데이터셋
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06528504B2

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