1'-benzhydryl-6-(benzyloxy)-2H-spiro[benzofuran-3,3'-indolin]-2'-one → 1'-(diphenylmethyl)-6-hydroxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 422842Notes

Reaction equation

HRID 422842 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]([CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:16]3=[O:37])C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[C:31]1([CH:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]3([C:12]4[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]=4[O:39][CH2:38]3)[C:16]2=[O:37])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 1

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

Product 1

HCID 593526351'-(diphenylmethyl)-6-hydroxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A suspension of 6-(benzyloxy)-1′-(diphenylmethyl)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (1.00 g, 2.0 mmol) in methanol/ethyl acetate (15/25 mL) was degassed by bubbling through nitrogen for 1 h before palladium on carbon (5%, 0.42 g, 0.2 mmol) was added. The mixture was stirred under hydrogen at ambient temperature for 16 h. The mixture was filtered through a pad of celite, and the filtrate was concentrated in vacuo. The obtained residue was recrystallized from ethyl acetate and hexane to afford 1′-(diphenylmethyl)-6-hydroxyspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (0.78 g, 95%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.42-7.25 (m, 10H), 7.16-7.10 (m, 1H), 7.07-6.92 (m, 3H), 6.54-6.48 (m, 1H), 6.44 (d, J=8.2 Hz, 1H), 6.33 (d, J=2.2 Hz, 1H), 6.20 (dd, J=8.2, 2.2 Hz, 1H), 5.65 (s, 1H), 4.99 (d, J=9.0 Hz, 1H), 4.71 (d, J=9.0 Hz, 1H); MS (ES+) m/z 420.1 (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 from ethyl acetate and hexane

Sources & evidence

ORD record
ord-0b35f47626ca4df5aec3c96d7ef825df
Source dataset
uspto-grants-2012_01
Patent number
US08101647B2

Reaction notes

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