Water → (S)-1-Benzyl-3-chloropyrrolidine

HRID 428590

반응식

HRID 428590 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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])(O)=O.[Na+].O.C(Cl)(Cl)(Cl)[Cl:40]>>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([Cl:40])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 5

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 643472(R)-(+)-1-Benzyl-3-pyrrolidinol

생성물 1

HCID 53640613(S)-1-Benzyl-3-chloropyrrolidine수율 72%

실험 절차

To a stirred solution of (R)-1-benzyl-3-pyrrolidinol (886 mg, 5.0 mmol) in CCl4(20 ml) was added triphenylphosphine(1.574 g, 6.0 mmol) at rt. After 20 h stirring at reflux temperature, the solvent was evapolated. Saturated NaHCO3 aqueous solution and water was added to the residue, and the mixture was extracted with AcOEt. The extract was brine, dried(Na2SO4), and concentrated to give brown oil, which was purified by column chromatography (silica gel; 100 g, CH2Cl2/MeOH: 50/1-45/1) to give 706 mg(72%) of pale yellow oil.

후처리

  1. temperatureat reflux temperature
  2. extractionthe mixture was extracted with AcOEt
  3. concentrationconcentrated
  4. customto give brown oil, which
  5. customwas purified by column chromatography (silica gel; 100 g, CH2Cl2/MeOH: 50/1-45/1)

출처 및 근거

ORD 기록
ord-6f249b707abc470fa69a44fb6b709c7c
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313302B2

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