HCID 46194180, compound → HCID 59352239, compound

HRID 1965694Notes

Reaction equation

HRID 1965694 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]2[C:15]3([CH2:30][O:31][C:11]=2[CH:10]=1)[C:23]1[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=1)[N:17]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:16]3=[O:29])C1C=CC=CC=1>[Pd].CO>[OH:8][C:9]1[CH:14]=[CH:13][C:12]2[C:15]3([CH2:30][O:31][C:11]=2[CH:10]=1)[C:23]1[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=1)[N:17]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:16]3=[O:29]

Participants

4

Reactant 1

HCID 46194180HCID 46194180, compound

Product 1

HCID 59352239HCID 59352239, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 6-(benzyloxy)-1′-(3-methylbutyl)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (7.80 g, 18.86 mmol) and 10% palladium on carbon (2.00 g, 1.88 mmol) in methanol (150 mL) was hydrogenated for 54 h. The mixture was filtered through a pad of celite, the filtrate was concentrated in vacuo, and the residue was crystallized from diethyl ether to give 6-hydroxy-1′-(3-methylbutyl)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (5.20 g, 85%) as a colorless solid: mp 101-103° C. (diethyl ether); 1H NMR (300 MHz, CDCl3) δ7.32-7.27 (m, 1H), 7.16-7.14 (m, 1H), 7.07-7.02 (m, 1H), 6.92-6.89 (m, 1H), 6.40-6.38 (m, 1H), 6.20-6.12 (m, 2H), 4.77 (AB, 2H), 3.86-3.70 (m, 2H), 1.64-1.59 (m, 3H), 0.99 (d, J=6.0 Hz, 6H); MS (ES+) m/z 324.3 (M+1).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-6951e1f36a394f4e9c7567848e91dbe3
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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