Methyl iodide → HCID 58612179, compound

HRID 1442642Notes

Reaction equation

HRID 1442642 reaction equation
CI.[N+:3]([C:6]1[CH:19]=[CH:18][C:9]([CH2:10][NH:11][CH2:12][C@H:13]2[CH2:17][CH2:16][CH2:15][O:14]2)=[CH:8][CH:7]=1)([O-:5])=[O:4].[C:20](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:20][N:11]([CH2:10][C:9]1[CH:8]=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:19][CH:18]=1)[CH2:12][C@H:13]1[CH2:17][CH2:16][CH2:15][O:14]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 26580537HCID 26580537, compound

Product 1

HCID 58612179HCID 58612179, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (0.728 mL, 11.7 mmol) was added to (4-nitro-benzyl)-[(2R)-tetrahydro-furan-2-ylmethyl]-amine Compound 10a2 (1.84 g, 7.80 mmol) and potassium carbonate (3.23 g, 23.4 mmol) in DMF (30 mL). After 4 hrs the reaction was diluted with water and extracted with ethyl ether. The combined extracts were washed with water, dried over MgSO4, and evaporated down to give 1.43 g of methyl-(4-nitro-benzyl)-[(2R)-tetrahydro-furan-2-ylmethyl]-amine Compound 10a3. Using the procedure of Example 21, Compound 10a3 was used in place of Compound 21a2 and carried forward to prepare 4-({methyl-[(2R)-tetrahydro-furan-2-ylmethyl]-amino}-methyl)-phenylamine Compound 10a.

Workup

  1. extractionextracted with ethyl ether
  2. washThe combined extracts were washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated down

Sources & evidence

ORD record
ord-ebadefbcbd634f22a6d67834cab1e080
Source dataset
uspto-grants-2010_02
Patent number
US07659284B2

Reaction notes

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