Hydrochloric Acid → 3-Benzyl-cis-3,7-diazabicyclo[3.3.0]octan-2,4-dione hydrochloride

HRID 857164Notes

Reaction equation

HRID 857164 reaction equation
[ClH:1].[CH2:2]([N:9]1[C:16](=[O:17])[C@@H:15]2[C@@H:11]([CH2:12][N:13](CC3C=CC=CC=3)[CH2:14]2)[C:10]1=[O:25])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N#N>CO.O.[Pd]>[ClH:1].[CH2:2]([N:9]1[C:10](=[O:25])[C@@H:11]2[C@@H:15]([CH2:14][NH:13][CH2:12]2)[C:16]1=[O:17])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 696631993,7-Dibenzyl-cis-3,7-diazabicyclo[3.3.0]octan-2,4-dione

Product 1

HCID 671476653-Benzyl-cis-3,7-diazabicyclo[3.3.0]octan-2,4-dione hydrochlorideYield 82%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Concentrated hydrochloric acid (28.4 mL, 341 mmol) was added to a suspension of 3,7-dibenzyl-3,7-diazabicyclo[3.3.0]octan-2,4-dione (109.0 g, 341 mmol; from step (a) above) in CH3OH under a N2 atmosphere. To the resulting solution there was added 10% Pd/C (w/w; 5 g). The N2 atmosphere was exchanged for H2 (1 atm of pressure) and the reaction was stirred for 12 h. The reaction was diluted with H2O (160 mL), filtered through a pad of cellulose to remove the catalyst and the filtrate concentrated in vacuo to afford a solid. Triturating with absolute EtOH afforded 74.6 g (82%) of the sub-title compound as an off-white solid after drying in a vacuum oven at 50° C./66.5 Pa (0.5 mm Hg).

Workup

  1. filtrationfiltered through a pad of cellulose
  2. customto remove the catalyst
  3. concentrationthe filtrate concentrated in vacuo
  4. customto afford a solid
  5. customTriturating with absolute EtOH

Sources & evidence

ORD record
ord-689d118d89da4304a28f667c441c3506
Source dataset
uspto-grants-2006_12
Patent number
US07144914B2

Reaction notes

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