2-(Dicyclohexylphosphino)biphenyl → 2-(6-Aminopyridin-3-yl)propan-2-ol

HRID 2069733ノート

反応式

HRID 2069733 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[Li][N:38]([Si](C)(C)C)[Si](C)(C)C>CCOC(C)=O.Cl>[NH2:38][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 27342162-(Dicyclohexylphosphino)biphenylHCID 125621182-(6-Chloropyridin-3-yl)propan-2-olHCID 178418261HCID 178418261、化合物

生成物 1

HCID 594737712-(6-Aminopyridin-3-yl)propan-2-ol収率 95.4%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

In a flame-dried seal tube reaction vial, under argon atmosphere, add 2-(6-Chloro-pyridin-3-yl)-propan-2-ol (750 mg, 4.375 mmol), 2-(dicyclohexylphosphino)-biphenyl (307 mg, 0.875 mmol) and then add LiN(TMS)2 (1M in THF, 13.5 mL, 13.5 mmol). Seal the tube and heat it up to 90° C. for 18 hours. The dark reaction mixture was then diluted with EtOAc (10 mL). HCl (2M) (10 drops) was added with stirring. The reaction mixture was then concentrated and loaded onto ISCO separation column and eluted with 5% MeOH/(1/1 EtOAC/Hex) to afford 2-(6-Amino-pyridin-3-yl)-propan-2-ol as solid (635 mg, yield 95%).

後処理

  1. customIn a flame-dried seal tube
  2. customreaction vial
  3. customSeal the tube
  4. customThe dark reaction mixture
  5. concentrationThe reaction mixture was then concentrated
  6. customloaded onto ISCO separation column
  7. washeluted with 5% MeOH/(1/1 EtOAC/Hex)

出典と根拠

ORDレコード
ord-cb20349881654a9293cce4a13ca3e69c
出典データセット
uspto-grants-2012_10
特許番号
US08299077B2

反応ノート

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