Ammonium Chloride → (S)-1-Azido-2-(5-bromo-2-fluoro-phenyl)-propan-2-ol

HRID 221727

反応式

HRID 221727 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([C@@:8]2([CH3:11])[CH2:10][O:9]2)[CH:7]=1.[N-:13]=[N+:14]=[N-:15].[Na+].[NH4+].[Cl-].C1OCCOCCOCCOCCOCCOC1>CCO>[N:13]([CH2:10][C@:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:12])([OH:9])[CH3:11])=[N+:14]=[N-:15]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 2855718-Crown-6HCID 33557Sodium AzideHCID 86650263(S)-2-(5-Bromo-2-fluoro-phenyl)-2-methyl-oxirane

生成物 1

HCID 86650264(S)-1-Azido-2-(5-bromo-2-fluoro-phenyl)-propan-2-ol

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of (S)-2-(5-bromo-2-fluoro-phenyl)-2-methyl-oxirane (51.85 g, 224 mmol) in EtOH (800 ml) was added NaN3 (36.8 g, 531 mmol), NH4Cl (60.6 g, 1122 mmol) and 18-crown-6 (59.8 g, 224 mmol) and the reaction mixture was heated at reflux for 6 h. The reaction mixture was filtered and concentrated to half of its volume. The residual oil was extracted with EtOAc. Combined extracts were washed with saturated NaHCO3 solution and brine, dried over MgSO4, filtered and concentrated to provide the title compound as a light yellow oil: TLC (hexane-EtOAc 1:1): Rf=0.70; HPLC RtH3=1.115 min; 1H NMR (360 MHz, CDCl3): δ 7.72 (dd, 1H), 7.32 (m, 1H), 6.85 (dd, 1H), 3.73 (d, 1H), 3.51 (d, 1H), 2.44 (s, 1H), 1.50 (s, 3H).

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 6 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated to half of its volume
  5. extractionThe residual oil was extracted with EtOAc
  6. washCombined extracts were washed with saturated NaHCO3 solution and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-803975ac2ec94edfad2fb9ae1a7c063e
出典データセット
uspto-grants-2012_06
特許番号
US08207164B2

関連ノート

読み込み中…