Methyl iodide → Tert-butyl 2-methyl-1-oxo-3-phenyl-2,6-diazaspiro[3.5]nonane-6-carboxylate

HRID 1036732Notes

Reaction equation

HRID 1036732 reaction equation
[O:1]=[C:2]1[C:5]2([CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]2)[CH:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:3]1.[H-].[Na+].I[CH3:27]>CN(C=O)C>[CH3:27][N:3]1[CH:4]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:5]2([CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]2)[C:2]1=[O:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71060527rac-tert-Butyl 1-oxo-3-phenyl-2,6-diazaspiro[3.5]nonane-6-carboxylate

Product 1

HCID 71060344Tert-butyl 2-methyl-1-oxo-3-phenyl-2,6-diazaspiro[3.5]nonane-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of rac-tert-butyl 1-oxo-3-phenyl-2,6-diazaspiro[3.5]nonane-6-carboxylate (1.18 g, 3.73 mmol) in DMF (20 ml) was cooled to 0° C. and treated with NaH (194 mg, 4.85 mmol) followed by iodomethane (303 ul, 4.85 mmol). The mixture was left to warm to room temperature. After 5 hours, the reaction was quenched with water and extracted with ethyl acetate. The organic layer was separated and washed with brine, dried (MgSO4) and concentrated in vacuo to yield a the title compound as a yellow oil;

Workup

  1. waitThe mixture was left
  2. customthe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-716b629e2a844ffda196e1267644840c
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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