Hydrochloric Acid → 1-((1S,4S)-2,5-diazabicyclo(2.2.1)heptan-2-yl)ethan-1-one hydrochloride
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]Participants
6
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
- concentrationThe reaction is concentrated
- dissolutionthe residue dissolved in DCM (15 mL)
- stirringThe reaction is stirred overnight
- filtrationthe solid filtered
Sources & evidence
- ORD record
- ord-f16f360f2a384a0ca84e5f47d0417ac9
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946203B2
Reaction notes
Loading…