Diisobutylaluminum hydride → (R)-2-((S)-3-benzyl-2-oxooxazolidin-4-yl)propanal

Temperature

-78 °C

To a solution of (R)-2-((S)-3-benzyl-2-oxooxazolidin-4-yl)-N-methoxy-N-methylpropanamide from Step 6 (1.5 g, 5.13 mmol) in THF (30 mL) was added dropwise DIBAL-H (1M solution in hexane; 11.29 mL) at −78° C. The mixture was stirred for 90 min at −78° C., diluted slowly with Rochelle's salt solution (1M solution in water; ˜20 mL) and stirred vigrously for ˜15 min. The aqueous layer was separated and extracted with ethyl acetate (3×). The combined organic extracts were washed with saturated sodium bicarbonate solution and brine, filtered through a mixture of celite/silica gel. The filtrate was concentrated under reduced pressure providing crude (R)-2-((S)-3-benzyl-2-oxooxazolidin-4-yl)propanal (1.26 g) as a colorless oil, which was directly used without further purification. MS m/z 234.2 (M+H)+; Rt-0.60 min.

1. stirringstirred vigrously for ˜15 min
2. customThe aqueous layer was separated
3. extractionextracted with ethyl acetate (3×)
4. washThe combined organic extracts were washed with saturated sodium bicarbonate solution and brine
5. filtrationfiltered through a mixture of celite/silica gel
6. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-c6909f475fd24092a14383f9de3b8147

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434719B2