Dimethylformamide → HCID 67073337, compound

HRID 2253041Notes

Reaction equation

HRID 2253041 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23]N(C)C=O.[H-].[Na+].CI>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:22][CH3:23])[CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67073062N-Boc-(R)-2-(3-(hydroxymethyl)benzyl)morpholine

Product 1

HCID 67073337HCID 67073337, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 0.20 g (0.65 mmol) (R)-2-(3-hydroxymethyl-benzyl)-morpholine-4-carboxylic acid tert-butyl ester in 3 mL N,N-dimethylformamide 31 mg (0.71 mmol; 55% dispersion in mineral oil) sodium hydride was added. After 30 min. 81 μL (1.3 mmol) methyl iodide was added. After 2 h the reaction mixture was diluted with ethyl acetate and extracted with 10% aqueous ammonium chloride solution followed by brine. The organic layer was dried over magnesium sulfate, filtered and evaporated and the residue was purified by column chromatography on silica gel with n-hexane:ethyl acetate (1:1) as eluant to give the title compound as a colorless oil (76%).

Workup

  1. extractionextracted with 10% aqueous ammonium chloride solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue was purified by column chromatography on silica gel with n-hexane:ethyl acetate (1:1) as eluant

Sources & evidence

ORD record
ord-0021047b21704cbdbe702d8576bc859f
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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