Water → 1-tert-Butyl 3-methyl 3-methyl-4-oxopiperidine-1,3-dicarboxylate

HRID 712198Notes

Reaction equation

HRID 712198 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]1[C:15]([O:17][CH3:18])=[O:16].[H-].[Na+].[CH3:21]I.O>CN(C=O)C>[CH3:21][C:3]1([C:15]([O:17][CH3:18])=[O:16])[C:2](=[O:1])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 112768931-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate

Product 1

HCID 667585171-tert-Butyl 3-methyl 3-methyl-4-oxopiperidine-1,3-dicarboxylateYield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of O1-tert-butyl O3-methyl 4-oxopiperidine-1,3-dicarboxylate (1 g, 3.88 mmol) in DMF (100 mL) was cooled to 0° C. followed by portion wise addition of NaH (60% dispersion of mineral oil, 0.16 g, 3.88 mmol). The resulting mixture was stirred at the same temperature for 15 min followed by addition of MeI (0.7 mL, 11.64 mmol) at 0° C. then stirred at rt for 44 h. After completion of reaction (by TLC), water (100 mL) was added and extracted with EtOAc (3×100 mL). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the product as a yellow oil (0.9 g). MS: 272.12 [M+H]+.

Workup

  1. stirringthen stirred at rt for 44 h
  2. additionwas added
  3. extractionextracted with EtOAc (3×100 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-32f6112067634da3847d522a81417dda
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

Loading…