Water → 2-(4-Bromophenyl)-5,8-dioxaspiro[3.4]octan-2-amine

HRID 1914843ノート

反応式

HRID 1914843 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(C(N)=O)[CH2:11][C:10]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:9]2)=[CH:4][CH:3]=1.O.FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.C([O-])(O)=O.[Na+].CC#[N:48]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH2:48])[CH2:11][C:10]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:9]2)=[CH:4][CH:3]=1

参加物

6

反応物 5

HCID 962WaterHCID 6342AcetonitrileHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 516892Sodium BicarbonateHCID 580344402-(4-Bromophenyl)-5,8-dioxaspiro[3.4]octane-2-carboxamide

生成物 1

HCID 582166022-(4-Bromophenyl)-5,8-dioxaspiro[3.4]octan-2-amine

実験手順

To a solution of Compound [XXXIV] (8.40 g, 26.9 mmol, 1.0 eq.) in CH3CN (26 mL) and water (26 mL) was added [bis(trifluoroacetoxy)iodo]benzene (17.4 g, 40.4 mmol, 1.5 eq.) and the resulting mixture stirred at room temperature. After 16 hours the reaction was slowly poured into NaHCO3 (aq sat) and extracted with ethyl acetate (×3). The combined organic layers were dried, concentrated, and the residue purified by silica gel chromatography by eluting with CHCl3 to CHCl3/MeOH/NH4OH (95:5:1) to give Compound [XXXV]: 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm 2.40-2.50 (m, 2H) 2.73-2.82 (m, 2H) 3.77-3.85 (m, 2H) 3.85-3.93 (m, 2H) 7.37-7.44 (m, 2H) 7.45-7.52 (m, 2H).

後処理

  1. extractionextracted with ethyl acetate (×3)
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customthe residue purified by silica gel chromatography
  5. washby eluting with CHCl3 to CHCl3/MeOH/NH4OH (95:5:1)

出典と根拠

ORDレコード
ord-1fabb254b2b1447ea212928f4124bb3c
出典データセット
uspto-grants-2013_12
特許番号
US08614221B2

反応ノート

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