Tricyclo(3.3.1.13,7)dec-1-ylmethylamine → HCID 59437162, compound

HRID 75154

Reaction equation

HRID 75154 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 59437162HCID 59437162, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0ecc176c213940abade3d063b7446509
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Linked notes

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