Iodoethane → HCID 69018277, compound

HRID 1437914Notes

Reaction equation

HRID 1437914 reaction equation
I[CH2:2][CH3:3].[CH3:4][C@@:5]12[C:22]([CH3:24])([CH3:23])[C@@H:8]([C:9]3[C:10](=[O:21])[N:11]([C:14]4[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=4)[NH:12][C:13]=31)[CH2:7][CH2:6]2.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH2:2]([N:12]1[C:13]2[C@@:5]3([CH3:4])[C:22]([CH3:24])([CH3:23])[C@H:8]([CH2:7][CH2:6]3)[C:9]=2[C:10](=[O:21])[N:11]1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)[CH3:3].[CH2:2]([O:21][C:10]1[N:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[N:12]=[C:13]2[C:9]=1[C@@H:8]1[C:22]([CH3:24])([CH3:23])[C@@:5]2([CH3:4])[CH2:6][CH2:7]1)[CH3:3]

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 57941413HCID 57941413, compound2×

Product 2

HCID 57941438HCID 57941438, compoundYield 7%HCID 69018277HCID 69018277, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Iodoethane (0.12 mL, 1.5 mmol) was added to (4S,7R)-7,8,8-trimethyl-2-p-tolyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 9; 400 mg, 1.4 mmol) and potassium carbonate (400 mg, 2.8 mmol) in dimethylformamide (5 mL). The mixture was heated at 60 degrees under argon overnight. The reaction mixture was diluted with water and extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, dried (magnesium sulfate), filtered, evaporated, and purified using an Analogix Intelliflash 280 system (Analogix, Inc., Burlington, Wis.) with an RS-12 column, eluting with 0-75% ethyl acetate/hexanes to give (4S,7R)-1-ethyl-7,8,8-trimethyl-2-p-tolyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (30 mg, 7%) as a white solid and (4S,7R)-3-ethoxy-7,8,8-trimethyl-2-p-tolyl-4,5,6,7-tetrahydro-2H-4,7-methano-indazole (266 mg, 60%) as a light yellow solid. ES(+)-MS (M+H) 311.

Workup

  1. temperatureThe mixture was heated at 60 degrees under argon overnight
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. custompurified
  8. washeluting with 0-75% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d311fd1722a34893b2a250f9038c4a6a
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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