Tricyclo(3.3.1.13,7)dec-1-ylmethylamine → 1-(4-(Benzyloxy)phenyl)-2-((1-adamantylmethyl)amino)ethanol

HRID 75147

Reaction equation

HRID 75147 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:17][O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]12([CH2:28][NH2:29])[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2>C(O)(C)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:16])[CH2:17][NH:29][CH2:28][C:18]23[CH2:27][CH:22]4[CH2:21][CH:20]([CH2:26][CH:24]([CH2:23]4)[CH2:25]2)[CH2:19]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 132487172-[4-(Benzyloxy)phenyl]oxirane

Product 1

HCID 594371761-(4-(Benzyloxy)phenyl)-2-((1-adamantylmethyl)amino)ethanolYield 23.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-(4-(benzyloxy)phenyl)oxirane (2 g, 8.8 mmol) and (1-adamantylmethyl)amine (1.46 g, 8.8 mol) were dissolved in isopropyl alcohol (30 mL) and heated under reflux overnight. The mixture was concentrated to give the crude product, which was purified by column chromatography to afford 1-(4-(benzyloxy)phenyl)-2-((1-adamantylmethyl)amino)ethanol (0.8 g, 23%). 1H NMR: (CDCl3, 400 MHz) δ=1.51 (m, 6H), 1.60-1.72 (m, 6H), 1.97 (m, 3H), 2.32&2.45 (dd, 2H), 2.64 (m, 1H), 2.73 (m, 1H), 2.94 (m, 1H), 3.40 (brs, 3H), 4.79 (m, 1H), 6.93 (m, 2H), 7.26-7.43 (m, 7H).

Workup

  1. temperatureheated
  2. temperatureunder reflux overnight
  3. concentrationThe mixture was concentrated
  4. customto give the crude product, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-88047b6c7522438b9fa11d82686d0f95
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Linked notes

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