Methyl iodide → HCID 16118896, compound

HRID 1437917Notes

Reaction equation

HRID 1437917 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16](=[O:17])[C:15]2[C@@H:14]3[C:18]([CH3:20])([CH3:19])[C@@:11]([CH3:21])([CH2:12][CH2:13]3)[C:10]=2[NH:9]1.[CH3:22]I>CN(C)C=O.O.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16](=[O:17])[C:15]2[C@@H:14]3[C:18]([CH3:20])([CH3:19])[C@@:11]([CH3:21])([CH2:12][CH2:13]3)[C:10]=2[N:9]1[CH3:22]

Participants

6

Reactant 2

HCID 6328Methyl iodideHCID 57941362HCID 57941362, compound2×

Product 1

HCID 16118896HCID 16118896, compoundYield 4.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (4S,7R)-2-(2-chloro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 10; 5.11 g, 16.9 mmol) and methyl iodide (1.05 mL, 16.9 mmol) in N,N-dimethylformamide (20 mL) was heated to 80° C. for 2 h. The reaction mixture was diluted with water (50 mL) and saturated sodium bicarbonate (150 mL) and extracted with ethyl acetate (2×200 mL). The organic extracts were combined, washed with brine, dried (sodium sulfate), filtered, evaporated, and purified using an ISCO CombiFlash® Sg100c chromatography system eluting with 10-100% ethyl acetate/hexanes to give (4S,7R)-2-(2-chloro-phenyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (233 mg, 4%). ES(+)-MS (M+H) 317.

Workup

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified
  7. washeluting with 10-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-73a69572f33e429090db350e8bc387d0
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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