Methyl iodide → HCID 59468940, compound

HRID 1690104Notes

Reaction equation

HRID 1690104 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:11]=[C:12]([C@H:16]2[CH2:20][CH2:19][C@:18]3([CH2:24][CH2:23][NH:22][C:21]3=[O:25])[N:17]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:13]=[CH:14][CH:15]=1.[H-].[Na+].[CH3:35]I>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:11]=[C:12]([C@H:16]2[CH2:20][CH2:19][C@:18]3([CH2:24][CH2:23][N:22]([CH3:35])[C:21]3=[O:25])[N:17]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59468914HCID 59468914, compound

Product 1

HCID 59468940HCID 59468940, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,1-dimethylethyl (2R,5R)-2-(3-{[(2-fluorophenyl)methyl]oxy}phenyl)-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate (D46, 60 mg, 0.14 mmol) in DMF (1 mL) cooled at 0° C., was added NaH (8 mg of a 60% dispersion in mineral oil, 0.20 mmol) in one portion. The ice-bath was removed and the reaction mixture left under stirring for 15 min. Methyl iodide (25 μL, 0.41 mmol) was added to the mixture and after 1 h the reaction was quenched with water. The aqueous layer was extracted with ethyl acetate, dried (Na2SO4) and evaporated. The crude material was purified by chromatography on silica gel using cyclohexane/ethyl acetate (7:3) affording the title compound (70 mg, quant.); Rt (HPLC): 6.03 min; MS: (ES/+) m/z: 477 [M+Na+]; C26H31FN2O4 requires 454.

Workup

  1. customThe ice-bath was removed
  2. waitthe reaction mixture left
  3. customwas quenched with water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-60a9a789da8442ffb330052320921654
Source dataset
uspto-grants-2012_04
Patent number
US08153623B2

Reaction notes

Loading…