Methyl iodide → HCID 178496579, compound

HRID 416002Notes

Reaction equation

HRID 416002 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:30]=[C:29]([Cl:31])[C:14]([CH2:15][C@@H:16]2[CH2:20][CH2:19][N:18]([C@H:21]3[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23][CH2:22]3)[C:17]2=[O:28])=[C:13]([Cl:32])[CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH3:34]>CN(C)C=O>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([Cl:32])[C:14]([CH2:15][C@@H:16]2[CH2:20][CH2:19][N:18]([C@H:21]3[CH2:22][CH2:23][C@H:24]([O:27][CH3:34])[CH2:25][CH2:26]3)[C:17]2=[O:28])=[C:29]([Cl:31])[CH:30]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178516684HCID 178516684, compound

Product 1

HCID 178496579HCID 178496579, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Suspend sodium hydride (0.45 g, 11.15 mmol) in 10 ml of dry dimethylformamide at 0° C. After stirring for 10 minutes, add the solution of (R)-3-(4-benzyloxy-2,6-dichloro-benzyl)-trans-1-(4-hydroxy-cyclohexyl)-pyrrolidin-2-one (2.50 g, 5.58 mmol) in 5 ml of dry dimethylformamide. Stir the resulting mixture for 15 minutes at 0° C. Add iodomethane (1.40 ml, 22.32 mmol) and allow the mixture to warm to room temperature. Stir the reaction at room temperature for an additional 12 hours then quench with water and filter the white precipitate. Dry under vacuum to recover 2.59 g of the title compound: MS (m/z): 462 (M+).

Workup

  1. customat 0° C
  2. stirringStir the resulting mixture for 15 minutes at 0° C
  3. stirringStir
  4. customthe reaction at room temperature for an additional 12 hours
  5. customthen quench with water
  6. filtrationfilter the white precipitate
  7. customDry under vacuum
  8. customto recover 2.59 g of the title compound

Sources & evidence

ORD record
ord-e632a1fc7db04e468f122a6a8b371cc5
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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