Trimethylsilyl iodide → HCID 57650311, compound

HRID 2063496Notes

Reaction equation

HRID 2063496 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[C:8]([CH3:27])=[N:9][O:10][C:11]=2[C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2C(OCC2C=CC=CC=2)=O)=[CH:4][CH:3]=1.I[Si](C)(C)C>ClCCl>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[C:8]([CH3:27])=[N:9][O:10][C:11]=2[C@H:12]2[CH2:16][CH2:15][CH2:14][NH:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 57650158HCID 57650158, compound

Product 1

HCID 57650311HCID 57650311, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-benzyl 2-(4-(4-chlorobenzyl)-3-methylisoxazol-5-yl)pyrrolidine-1-carboxylate (220 mg, 0.54 mmol) in dichloromethane (20 mL) at 0° C. was added iodotrimethylsilane (110 μL, 0.8 mmol). The reaction mixture was allowed to warm to room temperature, stirred for 3 h, concentrated in vacuo and diluted with ether (30 mL). The organic layer was extracted with 1M HCl (2×50 mL). The aqueous layer was basified with 6 M NaOH and extracted with dichloromethane (3×50 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford (R)-4-(4-chlorobenzyl)-3-methyl-5-(pyrrolidin-2-yl)isoxazole (110 mg, 74%). LCMS: calculated: 276, found (MH+): 277.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with ether (30 mL)
  3. extractionThe organic layer was extracted with 1M HCl (2×50 mL)
  4. extractionextracted with dichloromethane (3×50 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b2b2b443d15499eb6b758487acbf3e1
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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