Iodoethane → HCID 57941445, compound

HRID 1437993Notes

Reaction equation

HRID 1437993 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17](=[O:18])[C:16]3[C@@H:15]4[C:19]([CH3:21])([CH3:20])[C@@:12]([CH3:22])([CH2:13][CH2:14]4)[C:11]=3[NH:10]2)=[CH:5][CH:4]=1.I[CH2:24][CH3:25]>CN(C)C=O.ClCCl>[CH2:24]([N:10]1[C:11]2[C@@:12]3([CH3:22])[C:19]([CH3:21])([CH3:20])[C@H:15]([CH2:14][CH2:13]3)[C:16]=2[C:17](=[O:18])[N:9]1[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[CH3:25]

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 57941426HCID 57941426, compound2×

Product 1

HCID 57941445HCID 57941445, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

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 iodoethane (405 μL, 5.0 mmol) in dimethylformamide (9 mL) was heated in a sealed tube at ˜100° C. overnight. 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) was 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)-1-ethyl-2-(4-methoxy-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (152 mg, 46%) as a light yellow solid. APCI(+)-MS (M+H) 327.

Workup

  1. temperatureto cool to room temperature
  2. customtransferred to a round-bottomed flask
  3. customevaporated
  4. additionEthyl acetate (100 mL) was 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

Sources & evidence

ORD record
ord-0a65b8ef5b59408fb7eb83a575c5bd00
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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