Lithium tri-s-butylborohydride → 2-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-thiazol-5-yl)-propyl]amide

Temperature

-78 °C

To a solution of 2-methyl-propane-2-sulfinic acid [1-(2-methanesulfonyl-thiazol-5-yl)-prop-(Z)-ylidene]-amide (93 mg, 0.29 mmol) in tetrahydrofurane (5 mL) was added L-selectride (1 M in THF, 0.58 mL, 0.58 mmol) dropwise at −78° C. The reaction was stirred for 2.5 h at −78° C. The reaction mixture was quenched with sat. ammonium chloride solution (100 mL), and the layers were separated. The aqueous layer was extracted with ethyl acetate (2×10 ml). The organic layers were combined, washed with brine (10 ml), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in hexanes to yield 2-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-thiazol-5-yl)-propyl]-amide (80 mg, 86%) as an oil. Major diastereomer was 96.4% de by HPLC.

1. customThe reaction mixture was quenched with sat. ammonium chloride solution (100 mL)
2. customthe layers were separated
3. extractionThe aqueous layer was extracted with ethyl acetate (2×10 ml)
4. washwashed with brine (10 ml)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by silica gel chromatography
9. washeluting with a gradient of 0-100% ethyl acetate in hexanes

ORD record

ord-53c9490a317d4933bcb6e7b95b4ea201

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293917B2