Sodium borohydride → Methyl 4-hydroxytetrahydro-2H-thiopyran-3-carboxylate

A solution of methyl 4-oxotetrahydro-2H-thiopyran-3-carboxylate (3.00 g, 17.2 mmol) in THF (57 mL) was stirred at 0° C. Sodium borohydride (1.30 g, 34.4 mmol) was added and the resulting mixture was stirred at ambient temperature for 4 hours. The mixture was thermally stabilized with a water bath and carefully quenched with 1N aqueous HCl. The reaction mixture was then diluted with water and extracted with EtOAc (2×). The combined organic extracts were washed with water, brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford the title compound. The residue was carried forward without further purification.

1. customThe mixture was thermally stabilized with a water bath
2. customcarefully quenched with 1N aqueous HCl
3. additionThe reaction mixture was then diluted with water
4. extractionextracted with EtOAc (2×)
5. washThe combined organic extracts were washed with water, brine
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-94ccdaf0f4834ef28f29f14c32a6f05c

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394282B2