HCID 11613980, compound → HCID 11545770, compound

HRID 1868602Notes

Reaction equation

HRID 1868602 reaction equation
[C:1]([NH:5][CH2:6][CH:7]([OH:43])[CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14](=[O:42])[CH:15]=[C:16]([C:20]3[CH:25]=[C:24]([O:26]CC4C=CC=CC=4)[CH:23]=[C:22]([O:34]CC4C=CC=CC=4)[CH:21]=3)[O:17]2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([NH:5][CH2:6][CH:7]([OH:43])[CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14](=[O:42])[CH:15]=[C:16]([C:20]3[CH:21]=[C:22]([OH:34])[CH:23]=[C:24]([OH:26])[CH:25]=3)[O:17]2)=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11613980HCID 11613980, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 11545770HCID 11545770, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 7-(3-tert-butylamino-2-hydroxy-propoxy)-3′,5′-dibenzyloxy-flavone, 34 (1.0 g, 1.73 mmol) in dry methanol (60 mL) was added 40 mg 10% Pd/C. The reaction mixture was shaken in Parr hydrogenation assembly under hydrogen gas atmosphere at 60 lbs for 4 h after replacement of the air by nitrogen. The Pd/C was filtered and methanol evaporated on rotavapor under reduced pressure to provide 48. Yield 660 mg (96%); mp 153° C. (decomposes); MS (FAB) 400 (M++1); IR (KBr) 3401, 1618; 1H NMR (200 MHz, DMSO-d6) δ 7.98 (d, J=8.8 Hz, 1IH), 7.30 (s, 1H), 7.13 (d, J=8.8 Hz, 1H), 6.90 (d, J=1.2 Hz, 2H), 6.7 (s, 1H), 6.52 (s, 1H), 4.27-4.23 (m, 3H), 3.18-2.99 (m, 2H), 1.32 (s, 9H). Analysis Calcd for C22H25NO6: C, 66.15; H, 6.31; N, 3.51. Found: C, 66.19; H, 6.47; N, 3.43.

Workup

  1. filtrationThe Pd/C was filtered
  2. custommethanol evaporated on rotavapor under reduced pressure

Sources & evidence

ORD record
ord-dd264d376ec340d7ab7dca62fc3d3064
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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