Diisobutylaluminum hydride → 2-(1-(4-Chloro-3-methoxyphenyl)piperidin-4-ylidene)ethanol

A solution of methyl 2-(1-(4-chloro-3-methoxyphenyl)piperidin-4-ylidene)acetate (275 mg, 0.930 mmol) in anhydrous THF (3 mL) was cooled to −78° C. and then treated with DIBAL-H (3.72 mL of a 1.0 M solution in toluene, 3.72 mmol). The reaction was stirred at −78° C. for 2.5 h and then quenched with EtOAc. After it warmed to 0° C., the mixture was treated with saturated potassium sodium tartrate solution and stirred vigorously for 20 min. The resulting mixture was extracted with EtOAc. The extract was dried (Na2SO4) and concentrated to give a yellow oil, which was purified by flash chromatography (4 g silica gel cartridge and gradient elution with EtOAc/hexanes) to give 2-(1-(4-chloro-3-methoxyphenyl)piperidin-4-ylidene)ethanol (253 mg, 0.945 mmol, 102% yield) as a yellow oil. 1H-NMR (400 MHz, CDCl3) δ ppm 7.18 (1 H, d, J=8.79 Hz), 6.48 (1 H, d, J=16.92 Hz), 6.43 (1 H, s), 5.50 (1 H, t, J=7.03 Hz), 4.18 (2 H, d, J=7.03 Hz), 3.87 (3 H, s), 3.22 (4 H, dt, J=9.50, 5.68 Hz), 2.39-2.48 (2 H, m), 2.32-2.39 (2 H, m).

1. customquenched with EtOAc
2. temperatureAfter it warmed to 0° C.
3. additionthe mixture was treated with saturated potassium sodium tartrate solution
4. stirringstirred vigorously for 20 min
5. extractionThe resulting mixture was extracted with EtOAc
6. dry with materialThe extract was dried (Na2SO4)
7. concentrationconcentrated
8. customto give a yellow oil, which
9. customwas purified by flash chromatography (4 g silica gel cartridge and gradient elution with EtOAc/hexanes)

ORD record

ord-c34a7cb1d6d347198f40a03e9ec38025

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354432B2