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

HRID 1743701Notes

Reaction equation

HRID 1743701 reaction equation
[ClH:1].[CH2:2]([N:9]1[C:15](=[O:16])[CH:14]2[N:17](CC3C=CC=CC=3)[CH:11]([CH2:12][CH2:13]2)[C:10]1=[O:25])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N#N>CO.[Pd]>[ClH:1].[CH2:2]([N:9]1[C:10](=[O:25])[CH:11]2[NH:17][CH:14]([CH2:13][CH2:12]2)[C:15]1=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 947Nitrogen2×HCID 222356423,8-Dibenzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione hydrochloride

Product 1

HCID 222355873-Benzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione hydrochlorideYield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3,8-Dibenzyl-3,8-diazabicyclo[3.2.1]octan-2,4-dione hydrochloride (39 g, 0.11 mol; from step (c) above) was added to a suspension of 10% Pd/C (500 mg) in methanol (500 mL) under a blanket of N2. The N2 atmosphere was exchanged for H2 (one atmosphere of pressure). The reaction was stirred vigorously overnight. The catalyst was removed by filtration and the filtrate concentrated in vacuo to afford 28.3 g (96%) of the sub-title compound as a light tan solid.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-3c4ad034eee142efb32a2b5751132b07
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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