Potassium Carbonate → HCID 58260011, compound

HRID 422874Notes

Reaction equation

HRID 422874 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([CH2:24][O:25][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[N:10]([CH2:17][C@H:18]1[CH2:22][CH2:21][CH2:20][O:19]1)[C:9]3=[O:23].C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][C:34]([O:36][CH3:37])=[O:35]>CC(=O)CC>[CH3:37][O:36][C:34](=[O:35])[CH2:33][O:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([CH2:24][O:25][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[N:10]([CH2:17][C@H:18]1[CH2:22][CH2:21][CH2:20][O:19]1)[C:9]3=[O:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 59352744HCID 59352744, compound

Product 1

HCID 58260011HCID 58260011, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The mixture of 6-hydroxy-1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (0.42 g, 1.23 mmol), potassium carbonate (0.22 g, 1.60 mmol) and methyl bromoacetate (0.15 mL, 1.60 mmol) in 2-butanone (10 mL) was refluxed for 15 h. The reaction mixture was concentrated in vacuo to dryness. The residue was purified by flash chromatography with 25% ethyl acetate in hexanes to afford methyl({2′-oxo-1′-[(2R)-tetrahydrofuran-2-ylmethyl]-1′,2′-dihydrospiro[1-benzofuran-3,3′-indol]-6-yl}oxy)acetate (0.51 g, 87%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.33-7.26 (m, 1H), 7.15-7.00 (m, 3H), 6.64-6.59 (m, 1H), 6.51 (d, J=2.4 Hz, 1H), 6.36 (dd, J=8.4, 2.4 Hz, 1H), 4.95 (d, J=9.0 Hz, 1H), 4.72 (d, J=9.0 Hz, 1H), 4.59 (s, 2H), 4.32-4.24 (m, 1H), 3.99-3.66 (m, 7H), 2.07-1.84 (m, 3H), 1.78-1.64 (m, 1H); MS (ES+) m/z 409.9 (M+1), 447.9 (M+39).

Workup

  1. temperaturewas refluxed for 15 h
  2. concentrationThe reaction mixture was concentrated in vacuo to dryness
  3. customThe residue was purified by flash chromatography with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-765d7f8ab9594a4b928e01f5e086b194
Source dataset
uspto-grants-2012_01
Patent number
US08101647B2

Reaction notes

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