Trifluoroacetic acid → 3,8-diazabicyclo(3.2.1)octan-2-one

HRID 1498528Notes

Reaction equation

HRID 1498528 reaction equation
C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[C:10](=[O:16])[NH:11][CH2:12]2)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:9]12[NH:8][CH:13]([CH2:14][CH2:15]1)[CH2:12][NH:11][C:10]2=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 16638505tert-Butyl 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 124305893,8-diazabicyclo(3.2.1)octan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (108 mg, 0.48 mmol) in DCM (0.5 mL) at 0° C. was added dropwise, TFA (0.5 ml) and the reaction mixture stirred for 30 min. The reaction was warmed to RT and stirred for 1 h before being concentrated in vacuo and triturated with diethyl ether. The resultant residue was subjected to flash chromatography (Isolute NH2, 50% methanol in DCM) to give 3,8-Diaza-bicyclo[3.2.1]octan-2-one as a white solid (69 mg, quantitative). LCMS): RT=0.32 min, [M+H]+=127. 1H NMR 400 MHz (DMSO-d6) δ: 7.02 (1 H, br, s), 3.53 (1 H, m), 3.24 (1 H, dd, J=11.00, 4.14 Hz), 2.80-2.79 (1 H, m), 2.77 (1 H, m), 1.78 (3 H, m), 1.57-1.56 (1 H, m).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-6ba0be93e1c542baa8e640643092c7a0
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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