Water → HCID 57941506, compound

HRID 1437928Notes

Reaction equation

HRID 1437928 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:17](=[O:18])[C:16]2[C@@H:15]3[C:19]([CH3:21])([CH3:20])[C@@:12]([CH3:22])([CH2:13][CH2:14]3)[C:11]=2[NH:10]1.I[CH3:24].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:17](=[O:18])[C:16]2[C@@H:15]3[C:19]([CH3:21])([CH3:20])[C@@:12]([CH3:22])([CH2:13][CH2:14]3)[C:11]=2[N:10]1[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 57941475HCID 57941475, compound2×

Product 1

HCID 57941506HCID 57941506, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (4S,7R)-2-(2,6-dichloro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 15; 1.2 g, 3.6 mmol) and iodomethane (0.45 mL, 8.0 mmol) in N,N-dimethylformamide (20 mL) was heated to 80° C. and stirred for 4.5 h. The reaction mixture was allowed to cool and water (200 mL) was added. A solid precipitated. Water (100 mL) was added, and the mixture was extracted with ethyl acetate (200 mL). The organic layer was washed with saturated sodium bicarbonate and brine, dried (sodium sulfate), filtered, concentrated and purified by chromatography, eluting with 5-80% ethyl acetate/dichloromethane. Fractions containing the product were combined, evaporated, and recrystallized from ethyl acetate/hexanes to give (4S,7R)-2-(2,6-dichloro-phenyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (220 mg 18%) as a light tan solid. ES(+)-MS (M+H) 351

Workup

  1. temperatureto cool
  2. customA solid precipitated
  3. additionWater (100 mL) was added
  4. extractionthe mixture was extracted with ethyl acetate (200 mL)
  5. washThe organic layer was washed with saturated sodium bicarbonate and brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by chromatography
  10. washeluting with 5-80% ethyl acetate/dichloromethane
  11. additionFractions containing the product
  12. customevaporated
  13. customrecrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-de7bfcb9091a48ac8c7ac1a681c0a30a
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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