Hydrochloric Acid → (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane-2-carboxamide hydrochloride

HRID 1841977Notes

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.[Si]([N:19]=C=O)(C)(C)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]([NH2:19])=[O:5]

Participants

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 TMS-isocyanate (2.68 mL, 20.2 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 (P).

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-5287602752534f50a2ab4c46db36d70f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946203B2

Reaction notes

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