反应详情

To a solution of 3-benzyloxypropanoic acid (27.7 mmol) in propan-2-ol (40 mL) under nitrogen at 0° C. was added dropwise thionyl chloride (30.5 mmol). The reaction mixture was allowed to reach room temperature over 30 minutes and stirred at room temperature overnight. The mixture was diluted with CH2Cl2 and washed with a saturated solution of NaHCO3 and brine. The organic layer was dried on Na2SO4, filtered and concentrated under reduced pressure. The crude was diluted with isopropanol (80 mL) and Pd(OH)2 (20%, 1 g) in isopropanol was added. The system (reaction in a stainless steel reactor) was purged with nitrogen, vacuum and H2 and the reaction mixture was stirred under H2 atmosphere (3 bars) overnight at room temperature. The reaction mixture was filtered through autocup and the precipitate was washed with isopropanol. The filtrates were concentrated under reduced pressure and dried under vacuum pump to give the expected compound in 78% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.26 (d, J=6.31 Hz, 6H), 2.19 (brs, 1H), 2.54 (t, J=5.56 Hz, 2H), 3.86 (t, J=5.56 Hz, 2H), 5.06 (heptuplet, J=6.25 Hz, 1H).

1. washwashed with a saturated solution of NaHCO3 and brine
2. customThe organic layer was dried on Na2SO4
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. additionThe crude was diluted with isopropanol (80 mL) and Pd(OH)2 (20%, 1 g) in isopropanol
6. additionwas added
7. customThe system (reaction in a stainless steel reactor)
8. customwas purged with nitrogen, vacuum and H2
9. stirringthe reaction mixture was stirred under H2 atmosphere (3 bars) overnight at room temperature
10. filtrationThe reaction mixture was filtered through autocup
11. washthe precipitate was washed with isopropanol
12. concentrationThe filtrates were concentrated under reduced pressure
13. customdried under vacuum pump