Water → rac-(3R,4S)-1-benzylpyrrolidine-3,4-diol

HRID 366885

反応式

HRID 366885 の反応式
[CH2:1]([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:13].[OH2:14].C1(C)C=C(C)C=C(C)C=1S(O)(=O)=O.O.C1C=C(Cl)C=C(C(OO)=O)C=1>CC(C)=O>[CH2:1]([N:8]1[CH2:12][CH:11]([OH:13])[CH:10]([OH:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 5615061-Benzyl-2,5-dihydropyrroleHCID 15620344HCID 15620344、化合物

生成物 1

HCID 536645rac-(3R,4S)-1-benzylpyrrolidine-3,4-diol収率 85.9%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of 15.9 g (0.1 mol) of 1-benzyl-3-pyrroline, 56.7 g (0.24 mol) of 2-mesitylenesulfonic acid dihydrate (produced by Aldrich Chemical Co., Inc.), 15.0 g of water, and 60.0 g of acetone in a round flask reactor, 31.1 g (0.13 mol) of 70% m-CPBA (m-chloroperbenzoic acid produced by Tokyo Chemical Industry Co., Ltd.) was added with stirring and allowed to react for 10 hours at 40° C. without irradiation by lamps. After completion, acetone was evaporated under reduced pressure, neutralized by NaOH (aq), and extracted with toluene and water. After the solvent was evaporated under reduced pressure, 16.6 g of 1-benzyl-3,4-dihydroxypyrrolidine (yield 85.9%) was obtained.

後処理

  1. customto react for 10 hours at 40° C. without irradiation by lamps
  2. customAfter completion, acetone was evaporated under reduced pressure
  3. extractionextracted with toluene and water
  4. customAfter the solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-81f268dae646416187394c82c944510c
出典データセット
uspto-grants-2000_10
特許番号
US06130338

関連ノート

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