Dichloromethane → HCID 66781684, compound

To a stirred solution of [3-(2-oxopropyl)phenyl]acetonitrile (2.00 g, 11.5 mmol) and (R)-1-phenylethylamine (1.52 mL, 11.9 mmol) in DCM (50.0 mL) was added sodium triacetoxyborohydride (7.59 g, 35.8 mmol). The resulting mixture was stirred at room temperature overnight. Aqueous sodium hydroxide (1 M, 10 mL) and saturated aqueous sodium bicarbonate (20 mL) were added and the layers were separated. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was partially purified by silica gel chromatography (0-5% MeOH in DCM). The resulting material was dissolved in MeOH and acetyl chloride (0.5 mL) was added. This mixture was concentrated under reduced pressure and the residue was dissolved in MeOH (15 mL). Diisopropyl ether (30 mL) was added slowly to form a second layer on top of the solution. After standing at room temperature, the titled compound (2.0 g, 55% yield) precipitated and was collected by filtration.

1. customthe layers were separated
2. dry with materialThe organic layer was dried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customThe residue was partially purified by silica gel chromatography (0-5% MeOH in DCM)
6. dissolutionThe resulting material was dissolved in MeOH
7. additionacetyl chloride (0.5 mL) was added
8. concentrationThis mixture was concentrated under reduced pressure
9. dissolutionthe residue was dissolved in MeOH (15 mL)
10. additionDiisopropyl ether (30 mL) was added slowly
11. customto form a second layer on top of the solution
12. customAfter standing at room temperature

ORD record

ord-75e7ed815e714d0c8c1695469c1eb6f4

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08551978B2