反应详情

A solution of (1R)-1-(4-pyridinyl)ethanol (37 g, 0.3 mol, 78% ee) in MeOH (2 L) was charged with PtO2 (5 g) under nitrogen atmosphere followed by acetic acid (19 mL). The mixture was evacuated and purged with hydrogen several times and then stirred under an atmosphere of hydrogen for 2 d at room temperature. The mixture was filtered to remove catalyst and the filtrate was concentrated in vacuo and triturated with EtOAc to yield a cream-colored solid which was collected by filtration. The filter cake was dissolved in MeOH (500 mL) and 50% NaOH (15.8 g) was added. The resulting solution was stirred at 25° C. for 30 min and concentrated. The resulting solid was triturated with Et2O (700 mL) and stirred at 25° C. for 30 min, the solids were removed by filtration and the filtrate was dried over MgSO4 and filtered again. The final filtrate was concentrated to yield (1R)-1-(4-piperidinyl)ethanol (22 g, 57% yield) as a light beige solid. 1H NMR (400 MHz, CDCl3): δ 3.50 (quint, 1H, J=6.3 Hz), 3.13-3.01 (m, 2H), 2.61-2.47 (m, 2H), 1.88 (br, 2H), 1.84-1.73 (m, 1H), 1.63-1.52 (m, 1H), 1.41-1.27 (m, 1H), 1.23-1.05 (m, 2H), 1.13 (d, 3H, J=6.2 Hz).

1. customThe mixture was evacuated
2. custompurged with hydrogen several times
3. filtrationThe mixture was filtered
4. customto remove catalyst
5. concentrationthe filtrate was concentrated in vacuo
6. customtriturated with EtOAc
7. customto yield a cream-colored solid which
8. filtrationwas collected by filtration
9. dissolutionThe filter cake was dissolved in MeOH (500 mL)
10. addition50% NaOH (15.8 g) was added
11. stirringThe resulting solution was stirred at 25° C. for 30 min
12. concentrationconcentrated
13. customThe resulting solid was triturated with Et2O (700 mL)
14. stirringstirred at 25° C. for 30 min
15. customthe solids were removed by filtration
16. dry with materialthe filtrate was dried over MgSO4
17. filtrationfiltered again
18. concentrationThe final filtrate was concentrated