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

HRID 2069733노트

반응식

HRID 2069733 반응식
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

참가 물질

6

반응물 3

HCID 27342162-(Dicyclohexylphosphino)biphenylHCID 125621182-(6-Chloropyridin-3-yl)propan-2-olHCID 178418261HCID 178418261, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-cb20349881654a9293cce4a13ca3e69c
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299077B2

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