Ethyl Acetate → HCID 59352113, compound

HRID 1965690Notes

Reaction equation

HRID 1965690 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]3([CH2:27][O:26][C:25]4[CH:28]=[C:29]5[C:33](=[CH:34][C:24]3=4)[CH2:32][CH2:31][O:30]5)[C:16]2=[O:35])[CH2:9]1)C1C=CC=CC=1.C(OCC)(=O)C>CO.[OH-].[OH-].[Pd+2]>[CH3:1][N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]3([CH2:27][O:26][C:25]4[CH:28]=[C:29]5[C:33](=[CH:34][C:24]3=4)[CH2:32][CH2:31][O:30]5)[C:16]2=[O:35])[CH2:9]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 59352775HCID 59352775, compound

Product 1

HCID 59352113HCID 59352113, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

1′-[(4-Benzylmorpholin-2-yl)methyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (0.19 g, 0.41 mmol) was suspended in methanol (20 mL) and ethyl acetate (20 mL) in a steel bomb, then 20% palladium hydroxide on carbon (0.03 g, 0.04 mmol) was added. Hydrogenation was done at 120 psi in the steel bomb for 16 h. The reaction mixture was filtered through a pad of celite, and the filtrate was concentrated to dryness. The residue was purified by column chromatography (ethyl acetate/methanol/ammonia, 10:1:0.1) to afford 1′-[(4-methylmorpholin-2-yl)methyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1H)-one (0.015 g, 10%) as a colorless foam as the first fraction: 1H NMR (300 MHz, CDCl3) δ7.34-7.25 (m, 1H), 7.17-6.99 (m, 3H), 6.48 (s, 0.5H), 6.44 (s, 0.5H), 6.39 (s, 1H), 4.94-4.88 (m, 1H), 4.69-4.63 (m, 1H), 4.52 (t, J=8.7 Hz, 2H), 4.00-3.55 (m, 5H), 2.97 (t, J=8.7 Hz, 2H), 2.76 (d, J=8.4 Hz, 1H), 2.60 (d, J=8.4 Hz, 1H), 2.26 (s, 3H), 2.18-1.88 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 178.1, 178.0, 161.8, 161.7, 161.2, 161.18, 142.7, 142.67, 132.7, 132.6, 128.7, 128.6), 123.7, 123.6, 123.3, 123.2, 120.4, 120.3, 119.8, 119.7, 118.9, 118.8, 109.6, 109.4, 93.2, 93.16, 80.5, 80.4, 73.7, 73.6, 72.3, 66.8, 66.6, 58.3 58.0, 57.6, 54.7, 54.6, 46.4, 46.3, 43.2, 43.17, 29.0; MS (ES+) m/z 393.0 (M+1), and 1-(morpholin-2-ylmethyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (0.04 g, 26%) as a colorless foam as the second fraction: MS (ES+) m/z 379.0 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was purified by column chromatography (ethyl acetate/methanol/ammonia, 10:1:0.1)

Sources & evidence

ORD record
ord-c69fd47820ff4b85a1f22ea800b9c7b0
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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