Sodium borohydride → HCID 59441646, compound

Temperature

-10 °C

To MeOH (200 mL) was added 3-(3-methyl-4-nitrophenyl)-1-propylpyridinium iodide (9.4 g, 22.7 mmol). The solution was stirred at −10° C. for 10 min followed by the slow portionwise addition of solid NaBH4 (2.8 g, 68.1 mmol, Aldrich) over 5 min. The reaction was kept stirring at −10° C. for 1 h. The mixture was concentrated and diluted with Ethyl acetate (200 mL) before the addition of sat. NaHCO3 aq (150 mL). The organic phase was washed with brine, concentrated, and dried (Na2SO4). Purification via chromatography on SiO2 (0-10% MeOH/DCM) afforded 5-(3-methyl-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridine (5.0 g, 85% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.87 (t, J=7.3 Hz, 3 H), 1.48-1.57 (m, 2 H), 2.29 (td, J=5.7, 3.2 Hz, 2 H), 2.39-2.43 (m, 2 H), 2.51 (t, J=5.7 Hz, 2 H), 3.26 (d, J=1.8 Hz, 2 H), 3.94 (s, 3 H), 6.43 (ddd, J=3.8, 2.2, 2.0 Hz, 1 H), 7.10 (dd, J=8.5, 1.7 Hz, 1 H), 7.23 (d, J=1.8 Hz, 1 H), 7.83 (d, J=8.4 Hz, 1 H); ESIMS (M+H)+=261.

1. stirringThe reaction was kept stirring at −10° C. for 1 h
2. concentrationThe mixture was concentrated
3. additiondiluted with Ethyl acetate (200 mL) before the addition of sat. NaHCO3 aq (150 mL)
4. washThe organic phase was washed with brine
5. concentrationconcentrated
6. dry with materialdried (Na2SO4)
7. customPurification via chromatography on SiO2 (0-10% MeOH/DCM)

ORD record

ord-2f409a8642be418f91fcf61494205f72

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07981903B2