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

HRID 1914843Notes

Reaction equation

HRID 1914843 reaction equation
[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

Participants

6

Reactant 5

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

Product 1

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

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-1fabb254b2b1447ea212928f4124bb3c
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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