Water → (1S,3R)-3-(3-pyridyl)cyclopentanol

HRID 655164노트

반응식

HRID 655164 반응식
C([O:4][C@H:5]1[CH2:9][CH2:8][C@@H:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH2:6]1)(=O)C.[OH-].[Na+].O>CO>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C@@H:7]2[CH2:8][CH2:9][C@H:5]([OH:4])[CH2:6]2)[CH:11]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59486131(1S,3R)-3-(3-pyridyl)cyclopentyl acetate

생성물 1

HCID 59486133(1S,3R)-3-(3-pyridyl)cyclopentanol수율 92.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of (1S,3R)-3-(3-pyridyl)cyclopentyl acetate (5.43 g, 26.5 mmol) in MeOH (80 ml) was added 1N NaOH aq. (26 mL) at 4° C., and stirred for 2 h at same temperature. To the reaction mixture was added H2O and then extracted with CH2Cl2 four times, and the combined layers were dried over Na2SO4. After concentration under reduced pressure, the residue was purified by column chromatography (EtOAc) to yield (1S,3R)-3-(3-pyridyl)cyclopentanol (3.99 g, 92%) as colorless oil.

후처리

  1. extractionextracted with CH2Cl2 four times
  2. dry with materialthe combined layers were dried over Na2SO4
  3. concentrationAfter concentration under reduced pressure
  4. customthe residue was purified by column chromatography (EtOAc)

출처 및 근거

ORD 기록
ord-730b8cd6965147809e39876cf5f1b31e
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071591B2

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