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

HRID 655144ノート

反応式

HRID 655144 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 67133971trans-3-(2-Pyridyl)cyclopentanol収率 30%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-55a01f475c14459c984030718130a64c
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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