Hexane → HCID 10203509, compound

HRID 889141Notes

Reaction equation

HRID 889141 reaction equation
C[Si](C)(C)N[Si](C)(C)C.C([Li])CCC.CCCCCC.[F:21][C:22]1[CH:23]=[C:24]([CH2:28][N:29]2[CH2:34][CH2:33][CH:32]([CH2:35][CH2:36][C:37]([C:39]3[CH:40]=[C:41]4[C:46]5=[C:47]([CH2:49][CH2:50][N:45]5[C:44](=[O:51])[CH2:43][CH2:42]4)[CH:48]=3)=[O:38])[CH2:31][CH2:30]2)[CH:25]=[CH:26][CH:27]=1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:62])(=O)=O)=CC=1>O1CCCC1.O>[F:62][CH:36]([CH2:35][CH:32]1[CH2:31][CH2:30][N:29]([CH2:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([F:21])[CH:23]=2)[CH2:34][CH2:33]1)[C:37]([C:39]1[CH:40]=[C:41]2[C:46]3=[C:47]([CH2:49][CH2:50][N:45]3[C:44](=[O:51])[CH2:43][CH2:42]2)[CH:48]=1)=[O:38]

Participants

8

Reactant 5

HCID 8058HexaneHCID 13838HexamethyldisilazaneHCID 588007N-FluorobenzenesulfonimideHCID 9888392HCID 9888392, compoundHCID 178418339Butyllithium

Product 1

HCID 10203509HCID 10203509, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-20 °C

Procedure

Into a nitrogen-flushed, three-necked flask, a solution of 1,1,1,3,3,3-hexamethyldisilazane (1.38 g, 8.60 mmol) in tetrahydrofuran (50 ml) was placed and the resulting mixture was cooled in a dry ice/acetone bath. Thereto was added dropwise a solution of n-butyl lithium in hexane (1.6 M)(5.4 ml, 8.6 mmol) and then the resulting solution was stirred at −20° C. for 10 minutes. To this solution, which was cooled again in a dry ice/acetone bath, was added dropwise a solution of 8-[3-[1-[(3-fluorophenyl)methyl]-4-piperidinyl]-1-oxopropyl]-1,2,5,6-tetrahydro-4H-pyrrolo-[3,2,1-ij]quinolin-4-one (3.0 g, 7.1 mol), which was obtained in Example 1, in tetrahydrofuran (20 ml). The resulting mixture was stirred at −20° C. for 20 minutes and then cooled again in a dry ice/acetone bath. To this solution was added dropwise a solution of N-fluorobenzenesulfonimide (1.38 g, 8.6 mmol) in tetrahydrofuran (20) and the temperature was gradually raised to room temperature. The reaction mixture was mixed with water and was extracted with ethyl acetate. Then, the organic layer was washed with a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate, and concentrated to remove the solvent. The resulting residue was purified by column chromatography on silica gel (eluent: ethyl acetate) to obtain of the title substance as a colorless oily substance (42 mg).

Workup

  1. customInto a nitrogen-flushed
  2. temperaturethe resulting mixture was cooled in a dry ice/acetone bath
  3. temperatureTo this solution, which was cooled again in a dry ice/acetone bath
  4. stirringThe resulting mixture was stirred at −20° C. for 20 minutes
  5. temperaturecooled again in a dry ice/acetone bath
  6. temperaturethe temperature was gradually raised to room temperature
  7. extractionwas extracted with ethyl acetate
  8. washThen, the organic layer was washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried with anhydrous sodium sulfate
  10. concentrationconcentrated
  11. customto remove the solvent
  12. customThe resulting residue was purified by column chromatography on silica gel (eluent: ethyl acetate)
  13. customto obtain of the title substance as a colorless oily substance (42 mg)

Sources & evidence

ORD record
ord-2971f2b6d74040d2b5bc076baf1b0535
Source dataset
uspto-grants-2012_08
Patent number
US08252814B2

Reaction notes

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