Sodium Carbonate → 10-Azatricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien4-ol-hydrochloride
Reaction equation
FC(F)(F)C([N:5]1[CH2:15][CH:14]2[CH2:16][CH:7]([C:8]3[CH:9]=[CH:10][C:11]([OH:17])=[CH:12][C:13]=32)[CH2:6]1)=O.C([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)C.[ClH:32]>CO.O>[ClH:32].[CH:14]12[CH2:16][CH:7]([CH2:6][NH:5][CH2:15]1)[C:8]1[CH:9]=[CH:10][C:11]([OH:17])=[CH:12][C:13]2=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
2,2,2-Trifluoro-1-(4-hydroxy-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-ethanone (50 mg, 0.184 mmol) was dissolved in methanol/H2O (3/1, 5 mL), treated with Na2CO3(s) (40 mg, 0.369 mmol) and warmed to 65° C. for 2 hours. The mixture was concentrated, diluted with H2O and extracted with CH2Cl2 (3×20 mL) then dried through a cotton plug. Filtration through a Silica gel plug provided an oil (10% methanol/CH2Cl2) which was treated with 3N HCl ethyl acetate (3 mL) then concentrated, dissolved in a minimum of methanol which was saturated with Et2O and stirred. After 18 hours the white crystalline product was collected by filtration (10 mg, 26%). 1H NMR (400 MHz, CDOD3) δ 7.16 (d, J=8.0 Hz, 1H), 6.80 (d, J=2.0 Hz, 1H), 6.72 (dd, J=8.0, 2.0 Hz, 1H), 3.32–3.28 (4H), 3.09 (dd, J 14.5,12.0 Hz, 2H), 2.32 (m, 1H), 2.03 (d, J=11.0 Hz, 1H). APCI MS m/e 176.2 [(M+1)+]. M.p. 308 (dec.)° C.
Workup
- concentrationThe mixture was concentrated
- additiondiluted with H2O
- extractionextracted with CH2Cl2 (3×20 mL)
- customthen dried through a cotton plug
- filtrationFiltration through a Silica gel plug
- customprovided an oil (10% methanol/CH2Cl2) which
- concentrationthen concentrated
- dissolutiondissolved in a minimum of methanol which
- filtrationAfter 18 hours the white crystalline product was collected by filtration (10 mg, 26%)
Sources & evidence
- ORD record
- ord-7916d0f13ee14de4927639806a77245f
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07144882B2
Reaction notes
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