HCID 66970999, compound → HCID 66970991, compound

Temperature

0 °C

Crude 10a from above (4.124 g) was dissolved in dichloromethane (10 mL) and cooled in an ice-H2O bath. The solution was slowly treated with ice-cold trifluoroacetic acid (10 mL) and stirred at 0° C. for 1 h. The reaction was then concentrated under reduced pressure and the oil obtained re-dissolved in acetonitrile and re-concentrated under reduced pressure. The crude TFA salt was cooled in an ice-H2O bath and treated slowly with ice-cold 1.0 N NaOH (75 mL). The product was extracted into dichloromethane (2×75 mL) and the pooled extracts washed successively with H2O, saturated NaHCO3 and saturated brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to afford 1.223 g crude 3-(2-methoxyphenyl)-8-azabicyclo[3.2.1]oct-2-ene 10b as a pale amber oil, which was taken to the next step without further purification. LC/MS (RP-C18, 10-99% CH3CN/0.05% TFA gradient over 5 min) m/z 216.2 [M+H]+, retention time 1.75 min.

1. temperaturecooled in an ice-H2O bath
2. concentrationThe reaction was then concentrated under reduced pressure
3. customthe oil obtained
4. concentrationre-concentrated under reduced pressure
5. temperatureThe crude TFA salt was cooled in an ice-H2O bath
6. additiontreated slowly with ice-cold 1.0 N NaOH (75 mL)
7. extractionThe product was extracted into dichloromethane (2×75 mL)
8. washthe pooled extracts washed successively with H2O, saturated NaHCO3 and saturated brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-ea442214e4d34f8092b7582cad609b1e

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07880007B2