Methyl iodide → HCID 54235817, compound

HRID 2257993Notes

Reaction equation

HRID 2257993 reaction equation
[CH3:1]N(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C.[OH:20][C:21]12[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH:24]3[CH2:31][CH2:32][N:33]3[CH2:39][C@@H:38]4[C:40]([CH3:42])([CH3:41])[C@:35]([CH3:43])([CH2:36][CH2:37]4)[CH2:34]3)[CH2:22]1)[CH2:28]2.[H-].[Na+].CI.[Cl-].[NH4+]>O.CN(C=O)C>[CH3:1][O:20][C:21]12[CH2:22][CH:23]3[CH2:29][CH:27]([CH2:26][CH:25]([CH:24]3[CH2:31][CH2:32][N:33]3[CH2:39][C@@H:38]4[C:40]([CH3:42])([CH3:41])[C@:35]([CH3:43])([CH2:36][CH2:37]4)[CH2:34]3)[CH2:30]1)[CH2:28]2

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 70262,4,6-Tris((dimethylamino)methyl)phenolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 53679707HCID 53679707, compound

Product 1

HCID 54235817HCID 54235817, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DMF 3 ml solution of trans-(1S)-3-[2-(5-hydroxy-2-adamantyl)ethyl]-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane (compound No. 58,8) 113 mg was added in a DMF suspension 2.5 ml of sodium hydride (60%, oil dispersion) 41.0 mg at 0° C., and after changing the temperature to room temperature, the reaction mixture was stirred for 1.1 hour. Methyl iodide 70 gI was added to the reaction mixture and stirred at the same temperature for 20 hours. The reaction mixture was cooled to O@C, aqueous saturated ammonium chloride and water were added in this order, then extracted with chloroform. Organic layer was separated and solvent was distilled off in vacuo. Residue was purified by means of silica gel column chromatography to obtain trans (IS)-3-[2-(5-methoxy-2-adamantyl)ethyl]-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane. Yield: 33. gmg (Yield 29%).

Workup

  1. customto room temperature
  2. stirringstirred at the same temperature for 20 hours
  3. additionwere added in this order
  4. extractionextracted with chloroform
  5. customOrganic layer was separated
  6. distillationsolvent was distilled off in vacuo
  7. customResidue was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-8f818f37ae394818be9a830dfc8c0279
Source dataset
uspto-grants-1997_08
Patent number
US05658923

Reaction notes

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