1'-(diphenylmethyl)-6,7-dihydrospiro[benzo[1,2-b:4,5-b']difuran-3,3'-indol]-2'(1'H)-one → 6,7-dihydrospiro[benzo[1,2-b:4,5-b']difuran-3,3'-indol]-2'(1'H)-one

HRID 545854Notes

Reaction equation

HRID 545854 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3([CH2:20][O:19][C:18]4=[CH:21][C:22]5[CH2:26][CH2:25][O:24][C:23]=5[CH:27]=[C:17]34)[C:9]2=[O:28])C=CC=CC=1.[H][H]>C(O)(=O)C.[OH-].[Pd+2].[OH-]>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2([CH2:20][O:19][C:18]3=[CH:21][C:22]4[CH2:26][CH2:25][O:24][C:23]=4[CH:27]=[C:17]23)[C:9]1=[O:28]

Participants

5

Reactant 2

HCID 592633821'-(diphenylmethyl)-6,7-dihydrospiro[benzo[1,2-b:4,5-b']difuran-3,3'-indol]-2'(1'H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 592634256,7-dihydrospiro[benzo[1,2-b:4,5-b']difuran-3,3'-indol]-2'(1'H)-oneYield 71.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1′-(diphenylmethyl)-6,7-dihydrospiro[benzo[1,2-b:4,5-b′]difuran-3,3′-indol]-2′(1′H)-one (0.29 g, 0.65 mmol) and palladium hydroxide (0.10 g, 20% on activated carbon) in acetic acid (20.0 mL) was hydrogenated at 60° C. under normal pressure of hydrogen for 20 hours. The reaction mixture was filtered through celite and washed with acetone (50.0 mL). The filtrate was concentrated in vacuo to dryness to give the title compound (0.13 g, 69%): MS (ES+) m/z 280.2 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with acetone (50.0 mL)
  3. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-45e8e96e4d01418093f10a4f6cd2f104
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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