1-(4-(Benzyloxy)phenyl)-2-((1-adamantylmethyl)amino)ethanol → HCID 59437178, compound

HRID 75148Notes

Reaction equation

HRID 75148 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:29])[CH2:16][NH:17][CH2:18][C:19]23[CH2:28][CH:23]4[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]4)[CH2:20]2)[CH2:26]3)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[C:19]12([CH2:18][NH:17][CH2:16][CH:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[OH:29])[CH2:28][CH:23]3[CH2:22][CH:21]([CH2:27][CH:25]([CH2:24]3)[CH2:26]1)[CH2:20]2

Participants

4

Reactant 1

HCID 594371761-(4-(Benzyloxy)phenyl)-2-((1-adamantylmethyl)amino)ethanol

Product 1

HCID 59437178HCID 59437178, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(4-(benzyloxy)phenyl)-2-((1-adamantylmethyl)amino)ethanol (0.8 g, 2.05 mmol) in MeOH (10 mL) was added Pd(OH)2 (80 mg). The mixture was stirred at rt under H2 for 30 min. The mixture was filtered and concentrated to give 4-(2-((1-adamantylmethyl)amino)-1-hydroxyethyl)phenol (0.5 g, yield: 81%). 1H NMR: (CDCl3, 400 MHz) δ=1.53 (m, 6H), 1.65 (m, 6H), 1.97 (m, 3H), 2.26 & 2.36 (dd, 2H), 2.62&2.83 (dd, 2H), 4.60 (m, 1H), 6.78 (m, 2H), 7.22 (m, 2H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-61c61c68b6784983b5e88dab8d7be1b8
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Reaction notes

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