Methyl 1-(pyridin-4-yl)piperidine-4-carboxylate → (1-(Pyridin-4-YL)piperidin-4-YL)methanol

Temperature

0 °C

1-(4-Pyridinyl)piperidine-4-methanol was prepared using a procedure similar to the following: A solution of methyl N-(4-pyridinyl)isonipecotate (600 mg, 2.72 mmol) in tetrahydrofuran was added to a solution of lithium aluminum hydride (100 mg) in tetrahydrofuran (14 mL) cooled to 0° C. Upon consumption of the starting material (0.5-2 h), the mixture was treated with water (0.10 mL), 15% aqueous sodium hydroxide (0.10 mL), and water (0.30 mL). After 0.25 h, the mixture was sonicated for 0.25 h, then poured into a mixture of ethyl acetate, water, sodium tartrate, and potassium tartrate. The aqueous layer was extracted twice with ethyl acetate and the combined extracts were dried (magnesium sulfate), filtered, and concentrated in vacuo to yield 357 mg (68%) of 1-(4-pyridinyl)piperidine-4-methanol, which was used without further purification.

1. custom1-(4-Pyridinyl)piperidine-4-methanol was prepared
2. customUpon consumption of the starting material (0.5-2 h)
3. additionthe mixture was treated with water (0.10 mL), 15% aqueous sodium hydroxide (0.10 mL), and water (0.30 mL)
4. customthe mixture was sonicated for 0.25 h
5. additionpoured into a mixture of ethyl acetate, water, sodium tartrate, and potassium tartrate
6. extractionThe aqueous layer was extracted twice with ethyl acetate
7. dry with materialthe combined extracts were dried (magnesium sulfate)
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-16ce0a2d81114c179cc51945f6350e9a

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06689780B1