Sodium → HCID 21522752, compound

Temperature

25 °C

Under a nitrogen atmosphere, to a refluxing suspension of sodium (2.401 g, 104 mmol) in toluene (20 mL) at a temperature of about 115° C. was added dropwise over 30 min bicyclo[3.3.1]nonan-3-one oxime (QS, 1.60 g, 10 44 mmol) in 2-propanol (8 mL). The mixture was stirred at reflux for 2 hr. After addition of the oxime solution is completed, 2-propanol (3 mL) was added dropwise. The reaction mixture was heated to reflux until all of the Na was consumed followed by cooling to a temperature of about 25° C. The reaction mixture was then quenched by the addition of H2O (20 mL). The organic layer was separated, and washed twice with 1N HCl (30 mL each). The acidic solution was made alkaline by the addition of 2N NaOH (50 mL), and extracted thrice with Et2O (50 mL each). The organic layers were combined and washed with saturated NaCl (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give of bicyclo[3.3.1]non-3-ylamine QA. This compound was used in the next step without purification in 2-propanol solution.

1. temperatureat reflux for 2 hr
2. temperatureThe reaction mixture was heated
3. customwas consumed
4. customThe reaction mixture was then quenched by the addition of H2O (20 mL)
5. customThe organic layer was separated
6. washwashed twice with 1N HCl (30 mL each)
7. additionby the addition of 2N NaOH (50 mL)
8. extractionextracted thrice with Et2O (50 mL each)
9. washwashed with saturated NaCl (50 mL)
10. dry with materialThe organic layer was dried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo

ORD record

ord-dcade64e79604ffd8a326068d44e3a49

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846929B2