Tetrahydrofuran → Trifluoroacetic acid

HRID 2111529ノート

反応式

HRID 2111529 の反応式
[CH:1]([N:14]1[CH2:17][C:16](=[O:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:19][C:20]([Si](C)(C)C)([F:22])[F:21].[F-].[Cs+].C1[CH2:33][O:32]CC1>>[CH:1]([N:14]1[CH2:17][C:16]([C:20]([F:22])([F:21])[F:19])([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[C:33]([OH:32])([C:20]([F:22])([F:21])[F:19])=[O:18]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 25953Cesium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 37355581-(Diphenylmethyl)azetidin-3-one

生成物 2

HCID 6422Trifluoroacetic acidHCID 576391211-(Diphenylmethyl)-3-(trifluoromethyl)azetidin-3-ol

実験手順

To a solution of 1-benzhydryl-azetidin-3-one (400 mg, 1.69 mmol) in THF (5 mL), trifluoromethyltrimethylsilane (360 mg, 2.53 mmol) and cesium fluoride(390 mg, 2.57 mmol) were added. The reaction mixture was stirred at rt. for 1 hr. Then it was quenched with 5 mL saturated NH4Cl solution and tetrabutylammonium fluoride (200 mg) was added. The resulting reaction mixture was stirred at rt. for three days. It was then extracted with ether (3×20 mL). The organic layers were combined, dried (MgSO4) and concentrated to give an orange oil as crude product. It was then purified by Prep.HPLC column to afford a white solid as final product as TFA salt. (350 mg, 49% yield). Retention time: 1.442 min. 1H NMR (500 MHz, MeOD) δ ppm 3.92 (d, J=11.29 Hz, 2 H) 4.35 (d, J=11.60 Hz, 2 H) 5.44 (s, 1 H) 7.34-7.55 (m, 10 H).

後処理

  1. customThen it was quenched with 5 mL saturated NH4Cl solution and tetrabutylammonium fluoride (200 mg)
  2. additionwas added
  3. customThe resulting reaction mixture
  4. stirringwas stirred at rt
  5. waitfor three days
  6. extractionIt was then extracted with ether (3×20 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto give an orange oil as crude product
  10. customIt was then purified by Prep.HPLC column

出典と根拠

ORDレコード
ord-95f23482c76e47a4a6fa5bdd54386fba
出典データセット
uspto-grants-2009_04
特許番号
US07521442B2

反応ノート

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