Sodium Hydroxide → HCID 70230347, compound

1-(2-((2-(2-Fluorophenyl)-2-(2-methylphenyl)ethenyl)oxy)ethyl)-1,2,5,6-tetrahydro-3-pyridinecarboxylic acid methyl ester hydrochloride (2.18 g, 0.0049 mol, prepared similarly to the method described in Example 70) was dissolved in ethanol (24 ml) and 12 N sodium hydroxide solution (1.83 ml) was introduced at 5° C. The solution was stirred at room temperature for 2.5 h and stored at −10° C. for 18 h. The reaction mixture was evaporated to a residue after pH had been adjusted to 6.5 with 4 N hydrochloric acid solution. Water (20 ml) and ethyl acetate (50 ml) were added, the aqueous layer was separated and extracted again with ethyl acetate (25 ml). The combined ethyl acetate extracts was washed with saturated brine (40 ml), dried (MgSO4) and evaporated to a residue, which was co-evaporated with dichloromethane (3×40 ml). The residue (1.9 g) was dissolved in toluene (15 ml) and methanol (0.2 ml) was introduced followed by chlorotrimethylsilane (0.62 ml). The mixture was stirred for 18 h at room temperature and cooled to 0° C. for 2 h. The title compound (1.9 g, 91%) was obtained as white crystals.

1. waitstored at −10° C. for 18 h
2. customThe reaction mixture was evaporated to a residue after pH
3. additionWater (20 ml) and ethyl acetate (50 ml) were added
4. customthe aqueous layer was separated
5. extractionextracted again with ethyl acetate (25 ml)
6. washThe combined ethyl acetate extracts was washed with saturated brine (40 ml)
7. dry with materialdried (MgSO4)
8. customevaporated to a residue, which
9. dissolutionThe residue (1.9 g) was dissolved in toluene (15 ml)
10. additionmethanol (0.2 ml) was introduced
11. stirringThe mixture was stirred for 18 h at room temperature
12. temperaturecooled to 0° C. for 2 h

ORD record

ord-6726f5b6680c423ca014456c47f1c756

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06174898B1