[5-{(1R)-2-[(2-{4-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-hydroxyethyl}-2-(benzyloxy)phenyl]formamide → (5-{(1R)-2-[(2-{4-[2-(1-adamantyl)ethoxy]phenyl}ethyl)amino]-1-hydroxyethyl}-2-hydroxyphenyl)formamide

HRID 1925500Notes

Reaction equation

HRID 1925500 reaction equation
[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][CH2:23][C@@H:24]([C:26]4[CH:27]=[CH:28][C:29]([O:35]CC5C=CC=CC=5)=[C:30]([NH:32][CH:33]=[O:34])[CH:31]=4)[OH:25])=[CH:16][CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>CO.O1CCCC1.[Pd]>[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][NH:22][CH2:23][C@@H:24]([C:26]4[CH:27]=[CH:28][C:29]([OH:35])=[C:30]([NH:32][CH:33]=[O:34])[CH:31]=4)[OH:25])=[CH:18][CH:19]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

5

Reactant 1

HCID 86649159[5-{(1R)-2-[(2-{4-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-hydroxyethyl}-2-(benzyloxy)phenyl]formamide

Product 1

HCID 59624929(5-{(1R)-2-[(2-{4-[2-(1-adamantyl)ethoxy]phenyl}ethyl)amino]-1-hydroxyethyl}-2-hydroxyphenyl)formamideYield 38.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 26 (0.32 g, 0.56 mmol) in a mixture of methanol (5 mL) and tetrahydrofuran (5 mL) was added palladium on charcoal (10%, 0.03 g). The reaction mixture was hydrogenated at 40 psi for 3 days. The catalyst was filtered through Celite® and the solvent removed under reduced pressure. The crude was purified by chromatography eluting with chloroform/methanol (6:1) to give the title compound as a solid (0.102 g, 37%)

Workup

  1. filtrationThe catalyst was filtered through Celite®
  2. customthe solvent removed under reduced pressure
  3. customThe crude was purified by chromatography
  4. washeluting with chloroform/methanol (6:1)

Sources & evidence

ORD record
ord-a6becfff89394e6eaed903e779273a83
Source dataset
uspto-grants-2012_05
Patent number
US08178679B2

Reaction notes

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