Isopropyl iodide → HCID 68559815, compound

HRID 383903Notes

Reaction equation

HRID 383903 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH2:14][CH2:13][CH2:12][C:11]=13)[N:8]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:7]([CH3:23])([CH3:22])[C:6](=[O:24])[CH:5]2[CH3:25].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:36]1COC[CH2:37]1.I[CH:42](C)C>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH2:14][CH2:13][CH2:12][C:11]=13)[N:8]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[C:7]([CH3:23])([CH3:22])[C:6](=[O:24])[C:5]2([CH3:42])[CH2:25][CH2:36][CH3:37]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 23714775LiHMDS tetrahydrofuranHCID 59233346HCID 59233346, compound

Product 1

HCID 68559815HCID 68559815, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of tert-butyl 6-bromo-2,2,4-trimethyl-2,3,4,7,8,9-hexahydro-1H-cyclopenta[h]quinolin-3-one-1-carboxylate (300 mg) obtained in Example 1, 7) in toluene (3 ml) was cooled to −20° C., 1.0 M lithiumbis(trimethylsilyl)amide/THF solution (2.9 ml) was added dropwise and the mixture was stirred for 15 min. 2-Iodopropane (293 μl) was added, and the mixture was stirred at 70° C. for 13 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to normal phase chromatography (elution solvent hexane-ethyl acetate=20:1→10:1) to give the title compound (136 mg, 41%).

Workup

  1. stirringthe mixture was stirred at 70° C. for 13 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washThe residue was subjected to normal phase chromatography (elution solvent hexane-ethyl acetate=20:1→10:1)

Sources & evidence

ORD record
ord-1abd653f5557489c9aeb969145bd257b
Source dataset
uspto-grants-2013_02
Patent number
US08367695B2

Reaction notes

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