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

HRID 75154

반응식

HRID 75154 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0ecc176c213940abade3d063b7446509
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835426B2

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