Tricyclo(3.3.1.13,7)dec-1-ylmethylamine → N-(1-adamantylmethyl)-5-methyl-3-oxohexanamide

HRID 75154

反応式

HRID 75154 の反応式
[CH3:1][CH:2]([CH3:16])[CH2:3][C:4]([CH:6]1[C:11](=[O:12])OC(C)(C)OC1=O)=[O:5].[C:17]12([CH2:27][NH2:28])[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2>O1CCOCC1>[C:17]12([CH2:27][NH:28][C:11](=[O:12])[CH2:6][C:4](=[O:5])[CH2:3][CH:2]([CH3:1])[CH3:16])[CH2:24][CH:23]3[CH2:22][CH:21]([CH2:20][CH:19]([CH2:25]3)[CH2:18]1)[CH2:26]2

参加物

4

反応物 2

HCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 594371732,2-Dimethyl-5-(3-methylbutanoyl)-1,3-dioxane-4,6-dione

生成物 1

HCID 59437162N-(1-adamantylmethyl)-5-methyl-3-oxohexanamide収率 54.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A solution of 5-(3-methylbutanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (2.76 g, 12 mmol) and (1-adamantylmethyl)amine (2 g, 12 mmol) in anhydrous 1,4-dioxane (10 mL) was heated under reflux for 2 h. Solvent was removed in vacuo. The residue was diluted with EtOAc (50 mL), washed with water, aq K2CO3 and brine, dried over Na2SO4 and concentrated to dryness. The residue was purified by chromatography on a silica gel column eluted with 20:1 PE/EtOAc to give the N-(1-adamantylmethyl)-5-methyl-3-oxohexanamide (1.90 g, 54.4%). 1H NMR: (400 MHz, CDCl3): δ=0.92 (s, 3H), 0.96 (s, 3H), 1.54 (s, 7H), 1.62-1.73 (m, 9H), 1.98 (s, 4H), 2.12(m, 1H), 2.45(d, 2H), 2.95(d, 2H), 3.65(s, 2H).

後処理

  1. temperatureunder reflux for 2 h
  2. customSolvent was removed in vacuo
  3. additionThe residue was diluted with EtOAc (50 mL)
  4. washwashed with water, aq K2CO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by chromatography on a silica gel column
  8. washeluted with 20:1 PE/EtOAc

出典と根拠

ORDレコード
ord-0ecc176c213940abade3d063b7446509
出典データセット
uspto-grants-2014_09
特許番号
US08835426B2

関連ノート

読み込み中…