Water → HCID 14369013, compound

HRID 1596470Notes

Reaction equation

HRID 1596470 reaction equation
[CH2:1]([N:8]1[C:15](=O)[CH:14]2[C:17]([CH3:19])([CH3:18])[CH:10]([C:11](=O)[NH:12][C:13]2=O)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCOCC1>[CH2:1]([N:8]1[CH2:9][CH:10]2[C:17]([CH3:19])([CH3:18])[CH:14]([CH2:13][NH:12][CH2:11]2)[CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 12372676HCID 12372676, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14369013HCID 14369013, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-benzyl-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetraone (980 mg; 3.26 mmol; from step (c) above) in 1,4-dioxane (25 mL) was added dropwise to a suspension of lithium aluminium hydride (990 mg; 26.1 mmol) in 1,4-dioxane (30 mL) at 0° C. The mixture was refluxed overnight, cooled to 0° C. whereafter water (1.0 mL), 15% aqueous sodium hydroxide (1.0 mL), and more water (3.0 mL), were added sequentially. After stirring for 1 h at 0° C., the mixture was filtered through a small pad of Celite, washing the Celite cake with ethyl acetate (100 mL). The filtrate was evaporated to give the sub-title compound (676 mg; 85% crude yield) as a colourless oil which was used directly in the next step without further purification.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. additionwere added sequentially
  3. filtrationthe mixture was filtered through a small pad of Celite
  4. washwashing the Celite cake with ethyl acetate (100 mL)
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-1682833ab3be4083ac8b7199bf8f4daf
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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