Hydrogen Peroxide → cis-1-Methyl-3-phenyl-4-piperidinol

Participants

Reaction Conditions

Reaction Steps

The procedure of Example 1a. through 1e. is repeated. 25 ml of a 1.0 M solution of lithium tri-secondary-butylborohydride in THF are added dropwise over a 10-minute period to a solution of 3.79 g of 1-methyl-3-phenyl-4-piperidone and 20 ml of tetrahydrofuran (THF) (distilled over lithium aluminum hydride), maintained at 0° C. The mixture gradually warms to 15° C. after two hours of stirring and an additional 5 ml of borohydride reagent are added and the mixture is stirred 18 hours at room temperature under a nitrogen atmosphere. The mixture is then treated with 90 ml of 10 weight percent aqueous NaOH solution followed by 61 ml of 30 percent by weight aqueous H2O2 solution. The mixture is stirred for 18 hours at room temperature under a nitrogen atmosphere and is then extracted with ether and then CH2 Cl2. The organic extracts are combined and washed with saturated aqueous NaCl solution and dried over Na2SO4. The organic extracts are then filtered and concentrated in vacuo to a solid. The solid is triturated with petroleum ether, filtered and dried for 3 hours at 60° C. over P2O5. The solid product of cis-1-methyl-3-phenyl-4-piperidinol has a melting point s 127° C., 131°-133° C.

Provenance & Evidence