Methanol → Tricyclo(3.3.1.13,7)dec-1-ylmethylamine

HRID 75141

反応式

HRID 75141 の反応式
[C:1]12([C:11]([NH2:13])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(C)C.CO>C1COCC1>[C:1]12([CH2:11][NH2:13])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

参加物

5

反応物 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 21686Tricyclo(3.3.1.13,7)decane-1-carboxamide

生成物 1

HCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamine収率 59%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of admantane-1-carboxamide (2 g, 11.17 mmol) in THF (50 mL) was added BH3.Me2S (10.2 M, 3.4 mL, 34.7 mmol) under nitrogen. The mixture was heated at reflux overnight. The solution was cooled to rt. Methanol (20 mL) was added to the solution. The mixture was concentrated under vacuum to give crude product, which was purified by chromatography on silica gel to afford (1-adamantyl)methylamine (1.09 g, 59%). 1H NMR (CDCl3, 400 MHz): δ=1.44-1.96 (m, 15H), 2.30 (s, 2H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated under vacuum
  4. customto give crude product, which
  5. customwas purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-6ea67caa19ef43d084cf1bbdb95ce0e3
出典データセット
uspto-grants-2014_09
特許番号
US08835426B2

関連ノート

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