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

HRID 1859452ノート

反応式

HRID 1859452 の反応式
[CH3:1][N:2]([CH3:17])[C:3]1[CH:16]=[CH:15][C:6]([CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl.O>[CH3:17][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][C@H:11]([O:14][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:10]2)=[CH:15][CH:16]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69900648(S)-1-(4-dimethylaminophenethyl)-3-hydroxypyrrolidine

生成物 1

HCID 86585524(S)-1-(4-dimethylaminophenethyl)-3-methanesulfonyloxy-pyrrolidine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

(S)-1-(4-dimethylaminophenethyl)-3-hydroxypyrrolidine (320 mg, 1.37 mmol) was dissolved in dichloromethane (10 ml). Triethylamine (152 mg, 1.50 mmol) and methanesulfonyl chloride (164 mg, 1.43 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)-1-(4-dimethylaminophenethyl)-3-methanesulfonyloxy-pyrrolidine in the form of a light yellow oil (378 mg, 88%).

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. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-a6aea6b868d242b8895442c66ea8c458
出典データセット
uspto-grants-2003_03
特許番号
US06528504B2

反応ノート

読み込み中…