1'-[4-(benzyloxy)benzyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-2'(1'H)-one → HCID 59352445, compound

HRID 1965794Notes

Reaction equation

HRID 1965794 reaction equation
C([O:8][C:9]1[CH:36]=[CH:35][C:12]([CH2:13][N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]3([CH2:26][O:25][C:24]4[CH:27]=[C:28]5[C:32](=[CH:33][C:23]3=4)[CH2:31][CH2:30][O:29]5)[C:15]2=[O:34])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO.C(OCC)(=O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]3([CH2:26][O:25][C:24]4[CH:27]=[C:28]5[C:32](=[CH:33][C:23]3=4)[CH2:31][CH2:30][O:29]5)[C:15]2=[O:34])=[CH:35][CH:36]=1

Participants

5

Reactant 1

HCID 593523251'-[4-(benzyloxy)benzyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-2'(1'H)-one

Product 1

HCID 59352445HCID 59352445, compoundYield 94.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1′-[4-(benzyloxy)benzyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1H)-one (2.4 g, 5.1 mmol) and palladium on carbon (10% w/w, 0.49 g) in anhydrous methanol (10 mL) and ethyl acetate (50 mL) was hydrogenated at ambient temperature under a balloon pressure for 16 h. The mixture was filtered through a pad of diatomaceous earth The pad was washed with ethyl acetate (50 mL) and the filtrate was concentrated in vacuo. The residue was purified by column chromatography and eluted with a 25% to 50% gradient of ethyl acetate in hexanes to afford 1′-(4-hydroxybenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (1.86 g, 94%) as a colorless solid: mp 226-227° C.; 1H NMR (300 MHz, CDCl3) δ 7.25-7.13 (m, 4H), 7.06-6.99 (m, 1H), 6.87-6.82 (m, 1H), 6.78-6.72 (m, 2H), 6.44-6.41 (m, 2H), 5.27 (s, 1H), 4.88 (ABq, J=69.0, 15.3 Hz, 2H), 4.84 (ABq, J=82.9, 9.0 Hz, 2H), 4.55-4.46 (m, 2H), 2.96-2.86 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 178.2, 161.8, 161.3, 155.5, 142.1, 132.8, 128.8, 128.7, 127.5, 123.9, 123.5, 120.0, 119.9, 118.8, 115.8, 109.4, 93.3, 80.5, 72.4, 70.0, 57.8, 43.7, 28.9; MS (ES+) m/z 385.9 (M+1).

Workup

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth The pad
  2. washwas washed with ethyl acetate (50 mL)
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by column chromatography
  5. washeluted with a 25% to 50% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-937ca213010d4e0f8fda938a448f42bc
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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