反应详情

Sodium triacetoxyborohydride (118 mg, 0.56 mmol) was added to a solution of 4-(5-amino-benzooxazol-2yl)-1,4-diaza-bicyclo[3.2.2]nonane (52 mg, 0.20 mmol, prepared as in Example 39) and benzaldehyde (21 μL, 0.204 mmol) in 1,2-dichloroethane. The resulting mixture was allowed to stir at RT for a period of 3 h, at which time 2 mL of 1 N NaOH solution was added. The aqueous layer was extracted with CHCl3 (3×) and the combined organic layers were washed with water and brine and then dried (Na2SO4), filtered and concentrated. The crude residue was purified by chromatography (Biotage, 25M) eluting with 6% MeOH in CHCl3 containing 1 mL of NH4OH per L of eluent to give 37 mg of the title compound as an oil: 1H NMR (CDCl3, 400 MHz) δ 7.37-7.29 (m, 3H), 7.25-7.22 (m, 2H), 7.00 (d, 1H, J=8.7 Hz), 6.64 (d, 1H, J=2.1 Hz), 6.27 (dd, 1H, J=8.7, 2.1 Hz), 4.47-4.45 (m, 1H), 4.30 (s, 2H), 3.87 (t, 2H, J=5.8 Hz), 3.16-3.09 (m, 4H), 3.01-2.96 (m, 2H), 2.15-2.08 (m, 2H), 1.81-1.73 (m, 2H): 13C NMR (CDCl3, 100 MHz) δ 146.0, 145.1, 142.0, 139.8, 128.8, 127.7, 127.3, 108.8, 106.0, 100.6, 57.3, 50.1, 49.4, 46.5, 44,1, 27.0; MS (Cl) m/z 349.2 (M+1).

1. additionwas added
2. extractionThe aqueous layer was extracted with CHCl3 (3×)
3. washthe combined organic layers were washed with water and brine
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude residue was purified by chromatography (Biotage, 25M)
8. washeluting with 6% MeOH in CHCl3 containing 1 mL of NH4OH per L of eluent