Diisobutylaluminum hydride → HCID 68557045, compound

Temperature

-10 °C

A solution of ethyl 2-(1-(2,4-dichloro-5-methoxyphenyl)piperidin-4-yl)propanoate (94 mg, 0.26 mmol) in anhydrous THF (2.0 mL) was placed under nitrogen atmosphere, cooled to −10° C., and treated with DIBAL-H (0.780 mL of a 1.0 M solution in THF, 0.780 mmol). After 30 min, the cooling bath was removed and the reaction warmed to RT where it stirred for 2 h. After this time, the mixture was quenched by adding EtOAc (3 mL) and stirred vigorously for 20 min. The pH of the mixture was adjusted to pH 6 using 1 M HCl. Once at the prescribed pH, EtOAc (20 mL) was added and the mixture was stirred at RT overnight. At the conclusion of this period, the organic phase was separated, washed with brine, dried (MgSO4) and concentrated to give 2-(1-(2,4-dichloro-5-methoxyphenyl)piperidin-4-yl)propan-1-ol (88 mg, 0.277 mmol, quantitative) as a yellow oil. LC-MS: 318.19, [M+H]; tR=3.89 min (method b). 1H-NMR (400 MHz, CDCl3) δ ppm 7.32 (1 H, s), 6.59 (1 H, s), 3.87 (3 H, s), 3.62-3.69 (1 H, m), 3.52-3.59 (1 H, m), 3.36-3.44 (2 H, m), 2.53-2.63 (2 H, m), 1.70-1.78 (2 H, m), 1.54-1.62 (3 H, m), 1.49-1.53 (1 H, m), 0.96 (3 H, d, J=6.80 Hz).

1. customthe cooling bath was removed
2. temperaturethe reaction warmed to RT where it
3. customAfter this time, the mixture was quenched
4. additionby adding EtOAc (3 mL)
5. stirringstirred vigorously for 20 min
6. additionOnce at the prescribed pH, EtOAc (20 mL) was added
7. stirringthe mixture was stirred at RT overnight
8. customAt the conclusion of this period, the organic phase was separated
9. washwashed with brine
10. dry with materialdried (MgSO4)
11. concentrationconcentrated

ORD record

ord-7d98b59040124b539632640946b3433b

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354432B2