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

Temperature

0 °C

A solution of methyl N-(4-pyridyl)isonipecotate (600 mg, 2.72 mmol) in tetrahydrofuran was added to 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 the title compound, which was used without further purification.

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

ORD record

ord-b5e1b19ee4ef40d7b64c14433e8cf6d1

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313122B1