4-Acetylbiphenyl → HCID 43177456, compound

Titanium isopropoxide (4.4 g, 4.6 mL, and 15.5 mmol) was added to a stirred solution of 4-acetyl-biphenyl (1 g, 5.1 mmol) and glycine ethyl ester hydrochloride (2.2 g, 16.0 mmol) in MeOH (20 mL) and stirring continued at room temperature overnight. NaBH4 (800 mg, 20 mmol) was added in portion wise and the resulting mixture was stirred at room temperature for 10 hrs. The above mixture was quenched with 2N aqueous NH3 solution, filtered the solid precipitated. The filtrate was extracted with EtOAc, the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by column chromatography (using neutral alumina and 20% EtOAc in hexane as eluent) to afford 297 mg (21.67% yield) of (1-biphenyl-4-yl-ethylamino)-acetic acid methyl ester. 1H NMR (CDCl3): δ 7.64 (t, 4H), 7.5-7.3 (m, 5H), 3.9-3.8 (q, 2H), 3.7 (s, 3H), 3.4 (d, 2H), 1.5 (d, 3H).

1. stirringthe resulting mixture was stirred at room temperature for 10 hrs
2. customThe above mixture was quenched with 2N aqueous NH3 solution
3. filtrationfiltered the solid
4. customprecipitated
5. extractionThe filtrate was extracted with EtOAc
6. dry with materialthe organic layer was dried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customThe resulting residue was purified by column chromatography (using neutral alumina and 20% EtOAc in hexane as eluent)

ORD record

ord-c2b53b6efac14048bf7091c128b94ae0

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842696B2