反应详情

The product from Step 1 (0.64 g, 2.81 mmol) is suspended in methanol (20 mL) and water (2 mL). Palladium on carbon (0.065 g, 0.281 mmol) is added and the mixture is degassed with nitrogen for 10 min before sodium borohydride (0.15 g, 3.93 mmol) is added portion-wise. The reaction is cooled with an ice bath and after 30 mins warmed to room temperature and stirred for 16 h at room temperature. The palladium is filtered through celite and washed with methanol (3×30 mL). The filtrate is concentrated in vacuo and the residue partitioned between dichloromethane (100 mL) and water (10 mL). The aqueous layer is extracted with dichloromethane (5×50 mL+1 mL MeOH). The organic layers are combined, dried (MgSO4) and solvent removed in vacuo to give an orange oil (0.42 g, 77%). NMR (400 MHz, CDCl3) δ=2.47-2.60 (m, 4H), 2.64-2.66 (m, 2H), 3.62-3.72 (m, 4H), 3.77-3.83 (m, 2H), 4.76 (brs, 2H), 6.49 (s, H), 6.61 (s, 1H).

1. additionis added portion-wise
2. temperatureThe reaction is cooled with an ice bath and after 30 mins
3. filtrationThe palladium is filtered through celite
4. washwashed with methanol (3×30 mL)
5. concentrationThe filtrate is concentrated in vacuo
6. customthe residue partitioned between dichloromethane (100 mL) and water (10 mL)
7. extractionThe aqueous layer is extracted with dichloromethane (5×50 mL+1 mL MeOH)
8. dry with materialdried (MgSO4) and solvent
9. customremoved in vacuo