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Hydrochloric Acid → 1-((1S,4S)-2,5-diazabicyclo(2.2.1)heptan-2-yl)ethan-1-one hydrochloride

HRID 1841976
Notes
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Reaction equation

HRID 1841976 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][NH:11]2)=O)(C)(C)C.[C:15](OC(=O)C)(=O)C.[ClH:22].O1CCOCC1>C(Cl)Cl>[ClH:22].[C@H:9]12[CH2:14][C@H:12]([NH:11][CH2:10]1)[CH2:13][N:8]2[C:6](=[O:5])[CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 312751,4-DioxaneHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 574640501-((1S,4S)-2,5-diazabicyclo(2.2.1)heptan-2-yl)ethan-1-one hydrochloride

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
25 °C

Procedure

To a solution of (1S,4S)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (1.00 g, 5.04 mmol) in DCM (15 mL) is added acetic anhydride (0.52 mL, 5.55 mmol) and the reaction stirred at about 25° C. for 72 hours. The reaction is concentrated, and the residue dissolved in DCM (15 mL) and treated with 4M HCl in 1,4-dioxane (5.04 mL, 20.2 mmol). The reaction is stirred overnight, and the solid filtered to afford the title compound (O).

Workup

  1. concentrationThe reaction is concentrated
  2. dissolutionthe residue dissolved in DCM (15 mL)
  3. stirringThe reaction is stirred overnight
  4. filtrationthe solid filtered

Sources & evidence

ORD record
ord-f16f360f2a384a0ca84e5f47d0417ac9
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946203B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes