3-Benzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione → 3-Benzyl-3,8-diazabicyclo[3.2.1]octane

HRID 1478951Notes

Reaction equation

HRID 1478951 reaction equation
[CH2:1]([N:8]1[C:14](=O)[CH:13]2[NH:16][CH:10]([CH2:11][CH2:12]2)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH2:1]([N:8]1[CH2:14][CH:13]2[NH:16][CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 148395753-Benzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 124305943-Benzyl-3,8-diazabicyclo[3.2.1]octaneYield 52%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3-benzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione LXVI (0.00108 mol, 250 mg) in dry ether (2 mL) was added to a stirred suspension of LiAlH4 (122 mg, 0.00315 mol) in dry ether (8 mL) at 0° C. under nitrogen atmosphere. The reaction bath was allowed to return at room temperature and stirring was continued for 30 h. After completion of the reaction (checked by TLC), the reaction mixture was quenched with chilled water and then stirred for 1 h. The reaction mixture was diluted with ether (20 mL) and the organic layer was washed with water, dried over Na2SO4, concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, 60-120 mesh; EA-Hexane, 1:1) to afford the product LXVII in 52% yield.

Workup

  1. customto return at room temperature
  2. customAfter completion of the reaction (checked by TLC)
  3. customthe reaction mixture was quenched with chilled water
  4. stirringstirred for 1 h
  5. additionThe reaction mixture was diluted with ether (20 mL)
  6. washthe organic layer was washed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe crude residue was purified by column chromatography (silica gel, 60-120 mesh; EA-Hexane, 1:1)
  10. customto afford the product LXVII in 52% yield

Sources & evidence

ORD record
ord-ed50a00057fe4d4ba5e4125a6e736fcc
Source dataset
uspto-grants-2016_08
Patent number
US09404081B2

Reaction notes

Loading…