Methanol → 1-Butanol, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (3R)-

Temperature

-78 °C

The crude product from Example 545A (˜37 mmol) was dissolved in dichloromethane (100 mL). To this stirred solution, chilled to −78° C., was added dropwise a 1M solution of diisobutylaluminum hydride in dichloromethane (185 mL, 185 mmol). The reaction mixture was stirred at −78° C. for two hours, then it was allowed to warm to −30° C. and stirred an additional 0.5 hours. Methanol was then added carefully at −20° C. to quench any remaining hydride. The reaction mixture was then diluted with methyl tert-butylether (200 mL) and washed with aqueous sodium tartrate solution (4×100 mL) and brine (2×100 mL). The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give the crude title compound (6.3 g, 83%).

1. temperatureto warm to −30° C.
2. stirringstirred an additional 0.5 hours
3. customto quench any remaining hydride
4. additionThe reaction mixture was then diluted with methyl tert-butylether (200 mL)
5. washwashed with aqueous sodium tartrate solution (4×100 mL) and brine (2×100 mL)
6. dry with materialThe organic layer was dried (MgSO4)
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-d95dfdac47834e5a909d8af395664648

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07001895B2