Lithium tri-s-butylborohydride → HCID 121396362, compound

Temperature

-78 °C

To a solution of (5S)-5-propanoyltetrahydrofuran-2-one (compound 28c, 35 g, 246.5 mmol) was added L-selectride (320 mL, 320 mmol, 1 M in THF) at −78° C. under N2. After addition, the reaction mixture was stirred at −78° C. for 2 hours. The reaction mixture was then quenched with 2N HCl (200 mL) and extracted with EtOAc (400 mL) twice. The combined organic layers were washed with brine (100 mL), concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 1:7 to 1:3 EtOAc in petroleum ether) to afford 20 g of (5S)-5-(1-hydroxypropyl)tetrahydrofuran-2-one (compound 28d) as a yellow oil. (Refer to Eur. J. Med. Chem. 1997, 32, 617-623).

1. additionAfter addition
2. customThe reaction mixture was then quenched with 2N HCl (200 mL)
3. extractionextracted with EtOAc (400 mL) twice
4. washThe combined organic layers were washed with brine (100 mL)
5. concentrationconcentrated in vacuo
6. customthe residue was purified by column chromatography on silica gel (eluting with 1:7 to 1:3 EtOAc in petroleum ether)

ORD record

ord-30ed4b7cfb554161a616a912df98afd9

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09441008B2