Methyl iodide → HCID 71060643, compound

HRID 1036700Notes

Reaction equation

HRID 1036700 reaction equation
[O:1]=[C:2]1[NH:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:3]21[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][CH2:4]2.[H-].[Na+].I[CH3:27]>CN(C=O)C.O>[CH3:27][N:17]1[CH2:16][CH:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:3]2([CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][CH2:4]2)[C:2]1=[O:1]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71060252HCID 71060252, compound

Product 1

HCID 71060643HCID 71060643, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl 6-oxo-9-phenyl-2,7-diazaspiro[4.4]nonane-2-carboxylate (commercially available) (1 g, 3.16 mmol)) in DMF (50 mL) was cooled to 0° C. and treated with sodium hydride (126 mg, 3.16 mmol)). The reaction was left to stir at 0° C. for 30 minutes and iodomethane (198 uL, 3.16 mmol) was added. The reaction mixture was left to warm to room temperature. After 3 h 30 mins, the mixture was diluted with water (100 mL) and extracted with EtOAc (100 mL). The organic phase was dried (MgSO4), filtered and concentrated in vacuo to afford a yellow oil. Purification by chromatography on silica eluting with 0-10% MeOH in TBME afforded the following diastereomers:

Workup

  1. waitThe reaction was left
  2. waitThe reaction mixture was left
  3. temperatureto warm to room temperature
  4. waitAfter 3 h 30 mins
  5. extractionextracted with EtOAc (100 mL)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto afford a yellow oil
  10. customPurification by chromatography on silica eluting with 0-10% MeOH in TBME
  11. customafforded the following diastereomers

Sources & evidence

ORD record
ord-34f83d5dd9d641ebaba6c5dfe91f1902
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

Loading…