Diisobutylaluminum hydride → HCID 68557045, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence