Water → (S)-1-benzyl-3-fluoropyrrolidine

HRID 428587

반응식

HRID 428587 반응식
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10](O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[F-:25].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([F:25])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 86583595(R)-1-Benzyl-3-pyrrolidinol tosylate

생성물 1

HCID 20694590(S)-1-benzyl-3-fluoropyrrolidine수율 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of (R)-1-benzyl-3-pyrrolidinol-tosylate (3.06 g, 9.24 mmol) in THF (30 ml) was added 1.0M solution of tetrabutylammonium fluoride in THF (37.0 ml 37.0 mmol) at room temperature. After 1.5 h stirring at reflux temperature, water (150 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate (100mix2). The combined extract was washed with water, brine, dried (Na2SO4), and concentrated to give brown oil, which was purified by column chromatography (silica gel: 80 g, CH2Cl2/MeOH 50/1) to afford 1.18 g (71%) of brown oil.

후처리

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate (100mix2)
  3. extractionThe combined extract
  4. washwas washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give brown oil, which
  8. customwas purified by column chromatography (silica gel: 80 g, CH2Cl2/MeOH 50/1)

출처 및 근거

ORD 기록
ord-ea4de7219b4046fd92e2d8cd81bd5517
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313302B2

연결된 노트

불러오는 중…