Trimethylamine oxide → HCID 118161664, compound

HRID 2203674Notes

Reaction equation

HRID 2203674 reaction equation
[CH3:1][N+:2]([O-])([CH3:4])[CH3:3].[C@@H:6]12[C@@H:11]([C:12]3[N:16]([CH:17]([CH3:19])[CH3:18])[N:15]=[C:14]([I:20])[CH:13]=3)[C@@H:10]1[CH2:9][CH:8]=[CH:7]2.C([N-]C(C)C)(C)C.[Li+]>O1CCCC1.O>[I:20][C:14]1[CH:13]=[C:12]([C@H:11]2[C@@H:10]3[CH2:9][CH:8]4[C@H:7]([C@H:6]23)[CH2:3][N:2]([CH3:4])[CH2:1]4)[N:16]([CH:17]([CH3:19])[CH3:18])[N:15]=1

Participants

6

Reactant 3

HCID 1145Trimethylamine oxideHCID 2724682Lithium diisopropylamideHCID 118161757HCID 118161757, compound

Product 1

HCID 118161664HCID 118161664, compoundYield 4.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of trimethylamine oxide (717 mg, 9.55 mmol) and 5-((1S,5R,6S)-bicyclo[3.1.0]hex-2-en-6-yl)-3-iodo-1-isopropyl-1H-pyrazole (2.0 g, 6.4 mmol) in tetrahydrofuran (10 mL) under nitrogen was added lithium diisopropylamide (28 mmol). After 1 h at 0° C., the reaction mixture was diluted with water (50 mL), and the resulting solution was extracted with ethyl acetate (2×20 mL). The collected organic was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (17% ethyl acetate in petroleum ether) afforded a brown oil (110 mg, 4.7%). LCMS (ESI): [MH]+=372.2.

Workup

  1. extractionthe resulting solution was extracted with ethyl acetate (2×20 mL)
  2. washThe collected organic was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (17% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-130c5cd6a38646af8d4b9c3a485b3bfc
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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