Sodium Iodide → HCID 86655158, compound

HRID 391252Notes

Reaction equation

HRID 391252 reaction equation
Br[CH:2]([CH2:15][CH2:16][CH2:17][CH2:18]Br)[C:3]([O:5][C@H:6]([CH3:14])[C:7](=[O:13])[N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:4].[Na+].[I-].C(N(CC)CC)C.[CH3:29][O:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1>C(OCC)(=O)C.O.O1CCCC1>[CH3:29][O:30][C:31]1[CH:37]=[CH:36][C:34]([N:35]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:2]2[C:3]([O:5][C@@H:6]([CH3:14])[C:7](=[O:13])[N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:4])=[CH:33][CH:32]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 7732P-AnisidineHCID 8471TriethylamineHCID 86655159HCID 86655159, compound

Product 1

HCID 86655158HCID 86655158, compoundYield 120.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To (1R)-1-methyl-2-oxo-2-tetrahydro-1-H-1-pyrrolylethyl 2,6-dibromohexanoate (1.2 g, 3.0 mmol), NaI (0.9 g, 6.0 mmol), triethylamine (0.9 g, 9.0 mmol) and tetrahydrofuran (6 mL) were added. To the solution, p-methoxyaniline (443 mg, 3.6 mmol) and tetrahydrofuran (6 mL) were added. The mixture was stirred at 40° C. for 20 hours. To the mixture, water and ethyl acetate were added for extraction. The obtained extract was dried with anhydrous magnesium sulfate, and the solvent was removed away under reduced pressure in order to obtain 1.3 g of oil. The oil was purified with silica gel column using ethyl acetate to obtain 793 mg of white solid (2.2 mmol, yield: 73%, The diastereo ratio calculated by NMR analysis was 92:8.).

Workup

  1. extractionThe obtained extract
  2. dry with materialwas dried with anhydrous magnesium sulfate
  3. customthe solvent was removed away under reduced pressure in order

Sources & evidence

ORD record
ord-298ec92300304cfeb5b75aeabc30096d
Source dataset
uspto-grants-2013_02
Patent number
US08383833B2

Reaction notes

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