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

HRID 1845122ノート

反応式

HRID 1845122 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-682a5483668f44a180b39332bf9f274c
出典データセット
uspto-grants-2015_02
特許番号
US08946439B2

反応ノート

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