Sodium borohydride → trans-3-(2-Pyridyl)cyclopentanol

HRID 655144노트

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HRID 655144 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8]1.[BH4-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@H:7]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8]1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 594861153-(2-Pyridyl)cyclopentan-1-one

생성물 1

HCID 67133971trans-3-(2-Pyridyl)cyclopentanol수율 30%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 3-(2-pyridyl)cyclopentan-1-one (3.17 g, 19.7 mmol) in MeOH (80 ml) was added portionwise NaBH4 (745 mg. 19.7 mmol) at 0° C., and stirred for 2 h at room temperature. The reaction mixture was poured into ice-water and then extracted with EtOAc. The organic layer was dried over anhyd Na2SO4 followed by the removal of solvent. The crude product was purified by column chromatography (Hexane/EtOAc=1/1→1/3) to yield trans-3-(2-pyridyl)cyclopentanol (965 mg, 30%) as colorless oil.

후처리

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhyd Na2SO4
  3. customfollowed by the removal of solvent
  4. customThe crude product was purified by column chromatography (Hexane/EtOAc=1/1→1/3)

출처 및 근거

ORD 기록
ord-55a01f475c14459c984030718130a64c
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071591B2

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