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

HRID 1582394Notes

Reaction equation

HRID 1582394 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[C:20](=O)[CH:19]2[NH:22][CH:16]([CH2:17][CH2:18]2)[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CCOCC>[CH2:7]([N:14]1[CH2:20][CH:19]2[NH:22][CH:16]([CH2:17][CH2:18]2)[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=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 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred suspension of LiAlH4 (1.37 g, 36.1 mmol) in dry Et2O (23 mL) was added a solution of 3-benzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione (2.74 g, 11.9 mmol) in dry Et2O (27.5 mL) dropwise at 0° C. Then the mixture was refluxed for 46 h. After cooling down, the mixture was quenched with H2O (1.4 mL), 15% aq. NaOH (1.4 mL) and H2O (4.1 mL) successively, filtered through celite. The filtrate was concentrated in vacuo to provide a product (2.3 g, 96%) as a yellow oil. This product was used for the next reaction without purification.

Workup

  1. temperatureThen the mixture was refluxed for 46 h
  2. temperatureAfter cooling down
  3. customthe mixture was quenched with H2O (1.4 mL), 15% aq. NaOH (1.4 mL) and H2O (4.1 mL) successively
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e383b49460a64b5a846a8e59d45edf4d
Source dataset
uspto-grants-2004_05
Patent number
US06734306B2

Reaction notes

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