Pyridine → HCID 59451498, 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 acetyl chloride (1.1 mL, 15.5 mmol). The reaction mixture was stirred for 2 h at 0° C. Water was added (10 mL) and the organic phase was separated and washed with 1 N 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 (1.60 g, 65%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.33-7.44 (m, 5H), 6.14 (br. s., 1H), 5.05-5.12 (m, 1H), 4.65 (ABq, 2H), 3.69 (ABq, 2H), 2.04 (s, 3H).

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. washwashed with 1 N 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-b6790c5d2db044878ab6d2d7b4e9aac3

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304419B2