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

HRID 655149ノート

反応式

HRID 655149 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9db59f582b614807af6455db8a6fef68
出典データセット
uspto-grants-2011_12
特許番号
US08071591B2

反応ノート

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