Pyridine → HCID 59451451, compound

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 cyclopropanecarbonyl chloride (1.1 g, 10.1 mmol). The reaction mixture was stirred for 12 h at RT. Water (10 mL) was added and the organic phase was separated and washed with 1N HCl (20 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel flash column chromatography (5-50% EtOAc:hexanes) to give the title compound (1.84 g, 75%) as a translucent solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.31-7.44 (m, 5H), 6.33 (d, 1H), 5.07-5.15 (m, 1H), 4.66 (s, 2H), 3.71 (ABq, 2H), 1.33-1.42 (m, 1H), 0.97-1.09 (m, 2H), 0.79-0.90 (m, 2H). ES-LCMS: m/z 245.1 (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 12 h at RT
8. customthe organic phase was separated
9. washwashed with 1N HCl (20 mL)
10. dry with materialdried (Na2SO4)
11. filtrationfiltered
12. concentrationconcentrated
13. customThe residue was purified by silica gel flash column chromatography (5-50% EtOAc:hexanes)

ORD record

ord-f8ebbc5d51ff4fe3987a43eb384d0c7d

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304419B2