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

HRID 1859446
ノート
印刷プレビュー

反応式

HRID 1859446 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

(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%).

後処理

  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

出典と根拠

ORDレコード
ord-54bc0494b11a41cdafa7cdddfbc33338
出典データセット
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06528504B2

反応ノート

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