Sodium ethoxide → HCID 59450532, compound

Temperature

0 °C

The benzoyl ester from Step E (30 g, 93.168 mmol) was dissolved in anhydrous ethanol (300 mL) and cooled to 0° C. under nitrogen. A solution of EtONa in EtOH (46.6 mL, 93.200 mmol) was slowly added. The resulting solution was stirred at room temperature for 4 hr. Most of the solvent was removed and the residue was carefully partitioned between ethyl acetate (200 mL) and HCl (aq, 0.5 M, 300 mL) and extracted with ethyl acetate (200 mL). The combined organic solution was washed with brine (200 mL), dried with sodium sulfate, and evaporated. The crude product was purified on silica gel column (EtOAc/PE=1:20) and then chiral prep-HPLC to obtain the pure title compound (enantiomeric excess: >95%). 1H-NMR (400 MHz, CDCl3) δ 7.16 (d, J=8.4 Hz, 1H), 6.60-6.65 (m, 2H), 4.14 (q, J=7.2 Hz, 2H), 3.19-3.25 (m, 1H), 2.87-2.99 (m, 2H), 2.39-2.43 (m, 1H), 1.26 (t, J=7.2 Hz, 3H), 1.17-1.19 (m, 1H) ppm. MS: m/e 219.0 (M+1)+.

1. customMost of the solvent was removed
2. customthe residue was carefully partitioned between ethyl acetate (200 mL) and HCl (aq, 0.5 M, 300 mL)
3. extractionextracted with ethyl acetate (200 mL)
4. washThe combined organic solution was washed with brine (200 mL)
5. dry with materialdried with sodium sulfate
6. customevaporated
7. customThe crude product was purified on silica gel column (EtOAc/PE=1:20)

ORD record

ord-2e3395d691504aceb27d88b383f21353

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399507B2