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

HRID 366885

반응식

HRID 366885 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 5615061-Benzyl-2,5-dihydropyrroleHCID 15620344HCID 15620344, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-81f268dae646416187394c82c944510c
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130338

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