Water → Benzyl 3-hydroxycyclohexane-1-carboxylate

Temperatur

0 °C

To a 0° C. solution of benzyl 3-oxocyclohexanecarboxylate 1 (2.50 g, 10.8 mmol) in 55 mL of THF was added NaBH4 (814 mg, 21.5 mmol) portionwise. The reaction mixture was maintained at 0° C. for 20 min. Then water was slowly added to the reaction, and the reaction was diluted with Et2O. The resulting layers were separated and the aqueous layer was further extracted with Et2O. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. Purification of the resulting residue by flash chromatography (Biotage™ 40M 5-25% EtOAc/hexanes then 25-35% EtOAc/hexanes) afforded the title compound as a clear, colorless oil. LCMS: calculated for C14H18O3 234.29, observed m/e 235.0 (M+H)+ 256.9 (M+Na) (Rt 1.74/4 min).

1. customThe resulting layers were separated
2. extractionthe aqueous layer was further extracted with Et2O
3. washThe combined organic layers were washed with brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customPurification of the resulting residue by flash chromatography (Biotage™ 40M 5-25% EtOAc/hexanes

ORD-Eintrag

ord-0018eef19c5f44878ebcf8d0f9b3c558

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08895596B2