Methyl iodide → HCID 57941347, compound

Temperature

100 °C

A mixture of (4S,7R)-2-(4-methoxy-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 40; 300 mg, 1.0 mmol) and iodomethane (315 μL, 5.1 mmol) in dimethylformamide (9 mL) was heated in a sealed tube at ˜100° C. for 1 h 40 min. The reaction mixture was allowed to cool to room temperature, diluted with dichloromethane (100 mL), transferred to a round-bottomed flask and evaporated. Ethyl acetate (100 mL) and dichloromethane (50 mL) were added and the solution was washed with water, concentrated aqueous sodium thiosulfate (50 mL; 50% w/v), saturated aqueous sodium hydrogen carbonate (50 mL) and brine (50 mL). The solution was dried (magnesium sulfate), filtered, evaporated, and purified using a Biotage 40S system, eluting with 3% methanol/dichloromethane. Fractions homogeneous for the product were evaporated, co-evaporated with ethanol and dried under high vacuum to give (4S,7R)-2-(4-methoxy-phenyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (235 mg, 75%) as an off-white solid. APCI(+)-MS (M+H) 313.

1. temperatureto cool to room temperature
2. customtransferred to a round-bottomed flask
3. customevaporated
4. additionEthyl acetate (100 mL) and dichloromethane (50 mL) were added
5. washthe solution was washed with water, concentrated aqueous sodium thiosulfate (50 mL; 50% w/v), saturated aqueous sodium hydrogen carbonate (50 mL) and brine (50 mL)
6. dry with materialThe solution was dried (magnesium sulfate)
7. filtrationfiltered
8. customevaporated
9. custompurified
10. washeluting with 3% methanol/dichloromethane
11. customFractions homogeneous for the product were evaporated
12. customdried under high vacuum

ORD record

ord-340c4e757938476683b18a0f2f821bb0

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622492B2