HCID 68839471, compound → HCID 57559168, compound

Temperature

50 °C

To a solution of the product from Step 5 in a 2:1 mixture of ethanol/acetic acid (30 mL) was added palladium hydroxide on carbon powder (0.13 g, 10 wt. %). The mixture was degassed and shaken under an atmosphere of hydrogen (75 psi) at 50° C. for 12 hours. The mixture was cooled to room temperature, filtered through diatomaceous earth and the solids washed with ethanol. The filtrate was concentrated and the residue was dissolved in saturated sodium carbonate solution and extracted with chloroform (3×50 mL). The combined organic phases were dried over sodium sulfate and concentrated to afford 0.98 g (86.6%) of the product as a foam. 1H NMR (400 MHz, Methanol-d4) δ 4.49 (q, 1H), 4.20 (q, 1H), 3.86-3.67 (m, 2H), 3.61 (s, 3H), 3.28-3.21 (m, 1H), 3.19-3.09 (m, 1H), 2.96-2.87 (m, 1H), 2.74-2.64 (m, 1H), 2.63-2.47 (m, 2H), 2.38-2.23 (m, 2H). MS 278.3 (AP+, 100).

1. customThe mixture was degassed
2. temperatureThe mixture was cooled to room temperature
3. filtrationfiltered through diatomaceous earth
4. washthe solids washed with ethanol
5. concentrationThe filtrate was concentrated
6. dissolutionthe residue was dissolved in saturated sodium carbonate solution
7. extractionextracted with chloroform (3×50 mL)
8. dry with materialThe combined organic phases were dried over sodium sulfate
9. concentrationconcentrated

ORD record

ord-0f6e991ef32b409c8dc798de657913b8

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07485641B2