Hydrochloric Acid → cis-3-(1H-pyrazol-1-yl)cyclopentanol

HRID 655149노트

반응식

HRID 655149 반응식
[N:1]1([CH:6]2[CH2:10][CH2:9][C:8](=[O:11])[CH2:7]2)[CH:5]=[CH:4][CH:3]=[N:2]1.[BH4-].[Na+].Cl.C([O-])(O)=O.[Na+]>CO>[N:1]1([C@@H:6]2[CH2:10][CH2:9][C@H:8]([OH:11])[CH2:7]2)[CH:5]=[CH:4][CH:3]=[N:2]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 594861173-(1H-pyrazol-1-yl)cyclopentan-1-one

생성물 1

HCID 67133889cis-3-(1H-pyrazol-1-yl)cyclopentanol수율 73%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 3-(1H-pyrazol-1-yl)cyclopentan-1-one (14.09 g, 93.8 mmol) in MeOH (150 ml) was added portionwise NaBH4 (1.77 g. 46.8 mmol) at 0° C., and stirred for 30 min at room temperature. The reaction mixture was poured into 0.5M HCl and basified with sat. NaHCO3 aq. and then extracted with CH2Cl2. The organic layer was dried over anhyd Na2SO4 followed by the removal of solvent. The crude product was purified by column chromatography (Hexane/EtOAc=2/1→1/1) to yield cis-3-(1H-pyrazol-1-yl)cyclopentanol (10.41 g, 73%) as colorless oil.

후처리

  1. extractionextracted with CH2Cl2
  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=2/1→1/1)

출처 및 근거

ORD 기록
ord-9db59f582b614807af6455db8a6fef68
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071591B2

반응 노트

불러오는 중…