1'-benzhydryl-6-(benzyloxy)-2H-spiro[benzofuran-3,3'-indolin]-2'-one → HCID 59352621, compound

HRID 422841Notes

Reaction equation

HRID 422841 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]2[C:15]3([CH2:38][O:39][C:11]=2[CH:10]=1)[C:23]1[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=1)[N:17](C(C1C=CC=CC=1)C1C=CC=CC=1)[C:16]3=[O:37])C1C=CC=CC=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]2[C:15]3([CH2:38][O:39][C:11]=2[CH:10]=1)[C:23]1[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=1)[NH:17][C:16]3=[O:37]

Participants

5

Reactant 2

HCID 461941811'-benzhydryl-6-(benzyloxy)-2H-spiro[benzofuran-3,3'-indolin]-2'-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 59352621HCID 59352621, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A suspension of 6-(benzyloxy)-1′-(diphenylmethyl)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (0.60 g, 1.2 mmol) in methanol (20 mL) was degassed by bubbling through nitrogen for 1 h before palladium hydroxide on carbon (20%, 0.08 g, 0.12 mmol) was added. The mixture was stirred under 120 psi of hydrogen at 60° C. for 16 h. The mixture was filtered through a pad of celite, and the filtrate was concentrated in vacuo. The obtained residue was recrystallized with ethyl acetate and hexane to afford 6-hydroxy-2H-spiro[benzofuran-3,3′-indolin]-2′-one (0.25 g, 83%) as a colorless solid: 1H NMR (300 MHz, DMSO-d6) δ 10.86-9.35 (br, 2H), 7.19 (td, J=7.6, 1.2 Hz, 1H), 7.03 (d, J=7.3 Hz, 1H), 6.96-6.84 (m, 2H), 6.42 (d, J=8.2 Hz, 1H), 6.29 (d, J=2.1 Hz, 1H), 6.17 (dd, J=8.2, 2.1 Hz, 1H), 4.72 (d, J=9.2 Hz, 1H), 4.59 (d, J=9.2 Hz, 1H); MS (ES+) m/z 254.1 (M+1).

Workup

  1. customwas degassed
  2. additionwas added
  3. filtrationThe mixture was filtered through a pad of celite
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe obtained residue was recrystallized with ethyl acetate and hexane

Sources & evidence

ORD record
ord-2816f3b8e5e84208b397b4508213066e
Source dataset
uspto-grants-2012_01
Patent number
US08101647B2

Reaction notes

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