Sodium Iodide → HCID 86655156, compound

HRID 391251Notes

Reaction equation

HRID 391251 reaction equation
Br[CH:2]([CH2:15][CH2:16][CH2:17][CH3:18])[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.[CH3:28][O:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1.S([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.O1CCCC1>[CH3:28][O:29][C:30]1[CH:36]=[CH:35][C:33]([NH:34][CH:2]([CH2:15][CH2:16][CH2:17][CH3:18])[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:32][CH:31]=1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 7732P-AnisidineHCID 8471TriethylamineHCID 24437Sodium SulfiteHCID 86655157HCID 86655157, compound

Product 1

HCID 86655156HCID 86655156, compoundYield 150.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
37 °C

Procedure

To (1R)-1-methyl-2-oxo-2-tetrahydro-1-H-1-pyrrolylethyl 2-bromohexanoate (4.8 g, 15 mmol), NaI (2.3 g, 15 mmol), triethylamine (2.4 g, 24 mmol) and tetrahydrofuran (5 mL) were added. To the solution, p-methoxyaniline (2.4 g, 20 mmol) and tetrahydrofuran (5 mL) were added. The mixture was stirred at 37° C. for 1 hour and then at 20° C. for 5 hours. To the mixture, a saturated sodium sulfite aqueous solution and ethyl acetate were added for extraction. The obtained extract was dried with anhydrous magnesium sulfate, and then the solvent was removed away in reduced pressure in order to obtain 8.2 g of oil. The conversion ratio to the obtained compound was 1000, and the diastereo ratio calculated by NMR analysis was 94.5:5.5.

Workup

  1. waitat 20° C. for 5 hours
  2. extractionThe obtained extract
  3. dry with materialwas dried with anhydrous magnesium sulfate
  4. customthe solvent was removed away in reduced pressure in order

Sources & evidence

ORD record
ord-5e6636dc6ad3478894fa3a2aa03b98ea
Source dataset
uspto-grants-2013_02
Patent number
US08383833B2

Reaction notes

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