Isobutyraldehyde → a,a-diMethyl-1-Pyrrolidineacetaldehyde

HRID 1778423Notes

Reaction equation

HRID 1778423 reaction equation
[CH3:1][CH:2]([CH3:5])[CH:3]=[O:4].BrBr.[NH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1>C(Cl)Cl.[Cl-].[Na+].O>[CH3:1][C:2]([N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:5])[CH:3]=[O:4]

Participants

6

Reactant 3

HCID 6561IsobutyraldehydeHCID 24408BromineHCID 31268Pyrrolidine

Product 1

HCID 53867504a,a-diMethyl-1-Pyrrolidineacetaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-methylpropanal (5.6 mL, 61.8 mmol) in DCM (75 mL) cooled with an ice bath was added bromine (3.2 mL, 61.8 mmol) dropwise. After 1 hr, the solution was evaporated, stirred in DCM (8 ml) at room temperature and pyrrolidine (0.94 mL, 11.26 mmol) was added. After stirring 4 h, the mixture was diluted with brine and the layers separated. The organic layer was washed with 1M HCl and then the aqueous layer was basified with KOH to pH=10-11. This was then extracted with DCM and the organic layers were combined, dried (MgSO4), filtered and concentrated to isolate 2-methyl-2-pyrrolidin-1-yl-propanal oil as an oil.

Workup

  1. customthe solution was evaporated
  2. stirringAfter stirring 4 h
  3. customthe layers separated
  4. washThe organic layer was washed with 1M HCl
  5. extractionThis was then extracted with DCM
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-88c2c615450e46f998d68955aa6e6a6a
Source dataset
uspto-grants-2016_02
Patent number
US09266895B2

Reaction notes

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