Sodium Azide → (S)-2-Azido-2-(6-(trifluoromethyl)pyridin-3-yl)ethanol

HRID 1845122노트

반응식

HRID 1845122 반응식
[O:1]1[CH2:3][C@H:2]1[C:4]1[CH:5]=[CH:6][C:7]([C:10]([F:13])([F:12])[F:11])=[N:8][CH:9]=1.Cl([O-])(=O)(=O)=O.[Li+].[N-:20]=[N+:21]=[N-:22].[Na+]>C(#N)C>[N:20]([C@@H:2]([C:4]1[CH:9]=[N:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1)[CH2:3][OH:1])=[N+:21]=[N-:22]

참가 물질

5

반응물 3

HCID 33557Sodium AzideHCID 23665649Lithium perchlorateHCID 581880495-[(2R)-oxiran-2-yl]-2-(trifluoromethyl)pyridine

생성물 1

HCID 58188243(S)-2-Azido-2-(6-(trifluoromethyl)pyridin-3-yl)ethanol

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

To a stirred solution of (R)-5-(oxiran-2-yl)-2-(trifluoromethyl)pyridine (2.72 g, 14.4 mmol) in acetonitrile (200 mL) were added lithium perchlorate (20 g, 0.19 mol) and sodium azide (3.7 g, 57 mmol). The mixture was stirred at 60° C. overnight and TLC indicated completion of the reaction. After cooling, the mixture was filtered through Celite and the filtrate was concentrated. The residue was treated with water and extracted with EtOAc. The combined organic layers were dried, and concentrated. The residue was purified by silica gel column to afford the title compound.

후처리

  1. customcompletion of the reaction
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated
  5. additionThe residue was treated with water
  6. extractionextracted with EtOAc
  7. customThe combined organic layers were dried
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column

출처 및 근거

ORD 기록
ord-682a5483668f44a180b39332bf9f274c
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

반응 노트

불러오는 중…