Water → 3-Benzyl-3,8-diazabicyclo[3.2.1]octane

HRID 1031564Notes

Reaction equation

HRID 1031564 reaction equation
[CH2:1]([N:8]1[C:14](=O)[CH:13]2[N:16](C)[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-].[Al+3].[Li+].[H-].[H-].[H-].O>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

5

Reactant 3

HCID 962Water2×HCID 2868213-Benzyl-8-methyl-3,8-diazabicyclo[3.2.1]octane-2,4-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 124305943-Benzyl-3,8-diazabicyclo[3.2.1]octane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3-benzyl-2,4-dioxo-8-methyl-3,8-diazabicyclo (3.2.1)octane (2.05 g, 8.91 mmoles) in dry ether (100 mL) was treated gradually with lithium aluminum hydride (1.52 g, 4 mmoles), heated under reflux for one hour, and hydrolyzed successively with 50 mL of water-saturated ether and then 10 mL of water. This mixture was filtered on a celite pad. The filtrate was dried over magnesium sulfate and then evaporated to give the crude titled product which was used without any purification for further uses.

Workup

  1. temperatureheated
  2. temperatureunder reflux for one hour
  3. filtrationThis mixture was filtered on a celite pad
  4. dry with materialThe filtrate was dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-9a5202514472406590b1d792850caf73
Source dataset
uspto-grants-1990_09
Patent number
US04954507

Reaction notes

Loading…