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

HRID 75147

反応式

HRID 75147 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-88047b6c7522438b9fa11d82686d0f95
出典データセット
uspto-grants-2014_09
特許番号
US08835426B2

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