Water → (2S,3R,4S,5R)-5-((benzyloxy)methyl)-4-fluoro-2-methoxytetrahydrofuran-3-ol

HRID 2191044ノート

反応式

HRID 2191044 の反応式
[CH2:1]([O:8][CH2:9][C@H:10]1[O:15][C@H:14]([O:16][CH3:17])[C@@H:13]2[C@@H:11]1[O:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-:18].[Na+].O>C(O)CO>[CH2:1]([O:8][CH2:9][C@H:10]1[O:15][C@H:14]([O:16][CH3:17])[C@@H:13]([OH:12])[C@@H:11]1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 5235Sodium FluorideHCID 86641125HCID 86641125、化合物

生成物 1

HCID 11780118(2S,3R,4S,5R)-5-((benzyloxy)methyl)-4-fluoro-2-methoxytetrahydrofuran-3-ol収率 33%

試薬・触媒・溶媒 1

HCID 174Ethylene Glycol溶媒

反応条件

温度
200 °C

実験手順

Compound 35.7 (2.2 g, 9.32 mmol) was dissolved in 10 mL ethyleneglycol, and then treated with NaF (2.2 g), KHF2 (2.2 g). The mixture was stirred at 200° C. for 4 h, cooled to r.t. and then treated with water (150 mL). The aqueous mixture was extracted twice with 200 mL EtOAc. The organic extracts were combined, dried over MgSO4, filtered and concentrated down under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 20-100% EtOAc in hexane to give compound 35.8 (786 mg, 33% yield).

後処理

  1. temperaturecooled to r.t.
  2. extractionThe aqueous mixture was extracted twice with 200 mL EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated down under reduced pressure
  6. washeluting with 20-100% EtOAc in hexane

出典と根拠

ORDレコード
ord-20c1a4c8c9ed4e1398160e656d798f82
出典データセット
uspto-grants-2012_12
特許番号
US08324179B2

反応ノート

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