Methyl iodide → HCID 89720231, compound

A 15 mL seal tube fitted with magnetic stirrer was charged with 5 mL of THF, tert-butyl 5-hydroxy-2-azatricyclo[3.3.1.13,7]decane-2-carboxylate, Intermediate-6 (0.15 g, 0.5 mmol). Potassium hydride (47 mg, 1.1 mmol) was added to this mixture at 0° C., under N2 atm. The reaction mixture was then stirred at room temperature for 30 minutes. Methyl iodide was slowly added (0.12 g, 0.8 mmol) at 0° C. and the resulting reaction mass was refluxed at 60° C. under sealed condition for 12 hrs. After completion of the reaction (reaction was monitored by TLC), reaction mixture was quenched with cold water and extracted with ethyl acetate (25 ml×3). The organic layer was washed with sodium chloride solution, was dried over anhydrous sodium sulfate and was concentrated to give crude Intermediate-17, which was subjected to column chromatogram (22% EtOAc in PE) to obtain an oily mass (0.1 g, yield=70%).

1. customA 15 mL seal tube
2. customfitted with magnetic stirrer
3. customthe resulting reaction mass
4. temperaturewas refluxed at 60° C.
5. customunder sealed condition for 12 hrs
6. customAfter completion of the reaction (reaction was monitored by TLC), reaction mixture
7. customwas quenched with cold water
8. extractionextracted with ethyl acetate (25 ml×3)
9. washThe organic layer was washed with sodium chloride solution
10. dry with materialwas dried over anhydrous sodium sulfate
11. concentrationwas concentrated
12. customto give crude Intermediate-17, which
13. customto obtain an oily mass (0.1 g, yield=70%)

ORD record

ord-cb52a15b06254b33b966aab93435a572

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09303016B2