Water → (3-Methylpiperidin-3-yl)methanol

Temperature

-5 °C

To ethyl nipecotate (1.3 g) in THF (20 mL) at r.t was added potassium bis(trimethylsilyl)amide (18 mL of a 0.5 M solution in toluene). After 1 h, methyl iodide (0.5 mL) was added and the mixture was stirred for 15 h. Water was added and the mixture extracted with ether. The organics were washed with brine, dried and concentrated. The residual material (1.3 g) was dissolved in THF (20 mL) and treated with lithium aluminum hydride (8.7 mL of a 1 M solution in THF) at r.t. After 15 h, the mixture was cooled to -5° C. and aqueous sodium potassium tartrate was added followed by concentrated NH4OH, 10 N NaOH and the resulting mixture was stirred for 30 min. The mixture was filtered through anhydrous sodium sulfate and the filtrate was concentrated from toluene twice. The residual oil (1 g), containing the title compound, was used without further purification in Step 2.

1. extractionthe mixture extracted with ether
2. washThe organics were washed with brine
3. customdried
4. concentrationconcentrated
5. dissolutionThe residual material (1.3 g) was dissolved in THF (20 mL)
6. additiontreated with lithium aluminum hydride (8.7 mL of a 1 M solution in THF) at r.t
7. waitAfter 15 h
8. additionaqueous sodium potassium tartrate was added
9. stirringthe resulting mixture was stirred for 30 min
10. filtrationThe mixture was filtered through anhydrous sodium sulfate
11. concentrationthe filtrate was concentrated from toluene twice
12. additionThe residual oil (1 g), containing the title compound
13. customwas used without further purification in Step 2

ORD record

ord-fd4781567fb1477c8a384b27f708f0ee

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06004950