Réaction #10200

Équation de réaction

2,2,2-Trifluoro-1-(4-hydroxy-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-ethanone

Na2CO3

HCl ethyl acetate

→

10-Azatricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-4-ol hydrochloride

Solvants

methanol H2O

Conditions de réaction

Traitement

1. 1
   ConcentrationThe mixture was concentrated
2. 2
   workup.ADDITIONdiluted with H2O
3. 3
   Extractionextracted with CH2Cl2 (3×20 mL)
4. 4
   Autrethen dried through a cotton plug
5. 5
   FiltrationFiltration through a Silica gel plug
6. 6
   Autreprovided an oil (10% methanol/CH2Cl2) which
7. 7
   Concentrationthen concentrated
8. 8
   workup.DISSOLUTIONdissolved in a minimum of methanol which
9. 9
   FiltrationAfter 18 hours the white crystalline product was collected by filtration (10 mg, 26%)

Mode opératoire

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.

Source