Sodium Sulfite → 1-[3-Fluoro-6-(methoxy)-1,5-naphthyridin-4-yl]-1,2-ethanediol

HRID 639022

反応式

HRID 639022 の反応式
C(C1[C:4]([F:15])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13][CH3:14])[CH:9]=[CH:8]2)=C.S([O-])([O-])=O.[Na+].[Na+].[C:22]([OH:26])(C)([CH3:24])[CH3:23].[OH2:27]>>[F:15][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:23]=1[CH:22]([OH:26])[CH2:24][OH:27])=[N:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2

参加物

4

反応物 3

HCID 24437Sodium SulfiteHCID 575995778-Ethenyl-7-fluoro-2-(methoxy)-1,5-naphthyridineHCID 714019492-Methylpropan-2-ol--water (1/1)

生成物 1

HCID 671345911-[3-Fluoro-6-(methoxy)-1,5-naphthyridin-4-yl]-1,2-ethanediol収率 96%

実験手順

To a solution of AD-mixβ (50 g) in tert-butanol/water (200 mL/200 mL), cooled in an ice-bath for 30 minutes, 8-ethenyl-7-fluoro-2-(methyloxy)-1,5-naphthyridine (Preparation 6) (8 g, 39.2 mmol) was added and the reaction mixture was stirred at room temperature for 48 hours. Sodium sulfite (75 g) was added and the mixture was stirred for a further 30 minutes. It was extracted with diethyl ether then several times with 10% methanol in chloroform. The organic extract was evaporated under vacuum to afford the desired product as an oil (8.93 g, 96%). MS (+ve ion electrospray) m/z 239 (MH+); enantiomeric excess=44%, as determined by chiral analytical HPLC.

後処理

  1. stirringthe mixture was stirred for a further 30 minutes
  2. extractionIt was extracted with diethyl ether
  3. extractionThe organic extract
  4. customwas evaporated under vacuum

出典と根拠

ORDレコード
ord-e503c4dd0dbb4ff59358036b82935dda
出典データセット
uspto-grants-2010_04
特許番号
US07691850B2

関連ノート

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