5-{(1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-hydroxyethyl}-8-(benzyloxy)quinolin-2(1H)-one → 5-{(1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)amino]-1-hydroxyethyl}-8-hydroxyquinolin-2(1H)-one

HRID 1925504Notes

Reaction equation

HRID 1925504 reaction equation
[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][CH2:21][NH:22][CH2:23][C@@H:24]([C:26]4[CH:35]=[CH:34][C:33]([O:36]CC5C=CC=CC=5)=[C:32]5[C:27]=4[CH:28]=[CH:29][C:30](=[O:44])[NH:31]5)[OH:25])[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>[Pd]>[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][CH2:21][NH:22][CH2:23][C@@H:24]([C:26]4[CH:35]=[CH:34][C:33]([OH:36])=[C:32]5[C:27]=4[CH:28]=[CH:29][C:30](=[O:44])[NH:31]5)[OH:25])[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

3

Reactant 1

HCID 675206375-{(1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-hydroxyethyl}-8-(benzyloxy)quinolin-2(1H)-one

Product 1

HCID 426237805-{(1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)amino]-1-hydroxyethyl}-8-hydroxyquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Obtained from Intermediate 33 (0.365 g, 0.62 mmol) and palladium on charcoal (10%, 0.075 g) by the same procedure described in Example 1 (reaction time: 20 hours). The crude was purified by column chromatography with silica gel, eluting with methylen chloride/methanol/ammonium (40:2.5:0.1) and the title compound was obtained as a solid (0.113 g, 65%).

Workup

  1. customdescribed in Example 1 (reaction time: 20 hours)
  2. customThe crude was purified by column chromatography with silica gel
  3. washeluting with methylen chloride/methanol/ammonium (40:2.5:0.1)

Sources & evidence

ORD record
ord-fa7e09a429a540f7a93a6de757743e4d
Source dataset
uspto-grants-2012_05
Patent number
US08178679B2

Reaction notes

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