Hydrochloric Acid → (1S,4S)-2-(5-Benzoyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane dihydrochloride

HRID 23426Notes

Reaction equation

HRID 23426 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([N:15]2[CH2:20][C@@H:19]3[CH2:21][C@H:16]2[CH2:17][N:18]3C(OC(C)(C)C)=O)[CH:12]=[N:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:29]>C(OCC)(=O)C>[ClH:29].[ClH:29].[C:1]([C:9]1[CH:10]=[C:11]([N:15]2[CH2:20][C@@H:19]3[CH2:21][C@H:16]2[CH2:17][NH:18]3)[CH:12]=[N:13][CH:14]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68457814(1S,4S)-5-(5-Benzoyl-3-pyridyl)-2-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 68457220(1S,4S)-2-(5-Benzoyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane dihydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(1S,4S)-5-(5-Benzoyl-3-pyridyl)-2-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane (0.360 g, 0.95 mmol) was dissolved in ethyl acetate (30 mL). The solution was saturated with HCl gas at 5° C. (ice water bath) and was allowed to stand overnight at room temperature. After evaporation of the solvent under vacuum, the residue was triturated with ether. The formed precipitate was dried under vacuum to give 0.30 g (90%) of a yellow powder.

Workup

  1. customAfter evaporation of the solvent under vacuum
  2. customthe residue was triturated with ether
  3. customThe formed precipitate was dried under vacuum

Sources & evidence

ORD record
ord-e39bd02cb7d44de584290c3458fcbf4d
Source dataset
uspto-grants-2005_02
Patent number
US06852721B2

Reaction notes

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