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

Participants

Reaction Conditions

Reaction Steps

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%).

Provenance & Evidence