HCID 658603, compound → HCID 59570176, compound

3-tert-butyl-2-hydroxybenzaldehyde oxime (550 mg, 2.9 mmol) in EtOAc (10 mL) and MeOH (10 mL) was hydrogenated at balloon pressure in the presence of 10% Pd on carbon (100 mg) for 15 h. The reaction mixture was filtered over celite and concentrated. The residue was dissolved in EtOAc and 0.5 N HCl (10 mL). The layers were separated and the aqueous layer was treated with 1N NaOH solution until pH=9. The resulting aqueous layer was extracted with CHCl3 (3×10 mL). The combined CHCl3 was washed with brine, dried with Na2SO4 and concentrated under reduced pressure to provide to desired product (123 mg, 23%).

1. filtrationThe reaction mixture was filtered over celite and
2. concentrationconcentrated
3. dissolutionThe residue was dissolved in EtOAc
4. customThe layers were separated
5. additionthe aqueous layer was treated with 1N NaOH solution until pH=9
6. extractionThe resulting aqueous layer was extracted with CHCl3 (3×10 mL)
7. washThe combined CHCl3 was washed with brine
8. dry with materialdried with Na2SO4
9. concentrationconcentrated under reduced pressure

ORD record

ord-5de46f2656064f058ede2a6f43fd8643

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299267B2