Pyridine → 3-Benzyloxy-a-(N-butyryl)-aminopropionitrile

Benzyloxyacetaldehyde (1.5 g, 10.0 mmol) was added dropwise to a stirred solution of sodium cyanide (0.61 g, 12.4 mmol) and ammonium chloride (0.79 g, 14.8 mmol) in 25% ammonium hydroxide (5 mL). The solution was stirred at RT for 48 h, then extracted with CH2Cl2 (20 mL). The organic extract was washed with brine, dried (Na2SO4) and filtered. The filtrate was cooled to 0° C., and pyridine (1.3 mL, 16.1 mmol) was added followed by butyryl chloride (1.56 mL, 15.0 mmol). The reaction mixture was stirred for 2 h at 0° C. Water was added (10 mL) and the organic phase was separated, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel flash column chromatography (5-35% EtOAc:hexanes) to give the title compound (1.99 g, 81%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.32-7.43 (m, 5H), 6.09 (d, 1H), 5.08-5.14 (m, 1H), 4.64 (ABq, 2H), 3.71 (ABq, 2H), 2.20 (t, 2H), 1.62-1.73 (m, 2H), 0.96 (t, 3H). ES-LCMS: m/z 247.2 (M+1).

1. extractionextracted with CH2Cl2 (20 mL)
2. extractionThe organic extract
3. washwas washed with brine
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. temperatureThe filtrate was cooled to 0° C.
7. stirringThe reaction mixture was stirred for 2 h at 0° C
8. customthe organic phase was separated
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated
12. customThe residue was purified by silica gel flash column chromatography (5-35% EtOAc:hexanes)

ORD record

ord-3c45d961c0594ba99ee5c712d3e4d610

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304419B2