Formaldehyde → (Racemic)-N-[4-[3-(Acetyloxy)-1-pyrrolidinyl]-2-butynyl]-N-methyl acetamide

HRID 1710135Notes

Reaction equation

HRID 1710135 reaction equation
[C:1]([O:4][CH:5]1[CH2:9][CH2:8][NH:7][CH2:6]1)(=[O:3])[CH3:2].[CH3:10][N:11]([CH2:15][C:16]#[CH:17])[C:12](=[O:14])[CH3:13].C=O.[C:20](=O)(O)[O-].[Na+]>ClCCl.O1CCOCC1.C(O)(=O)C>[C:1]([O:4][CH:5]1[CH2:9][CH2:8][N:7]([CH2:20][C:17]#[C:16][CH2:15][N:11]([CH3:10])[C:12](=[O:14])[CH3:13])[CH2:6]1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 29033Acetamide, N-methyl-N-[2-propynyl]-HCID 516892Sodium BicarbonateHCID 15046662Pyrrolidin-3-yl acetate

Product 1

HCID 15086787(Racemic)-N-[4-[3-(Acetyloxy)-1-pyrrolidinyl]-2-butynyl]-N-methyl acetamide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.17 g of 3-acetoxy pyrrolidine, 1.2 g of N-methyl-N-propargyl acetamide, 465 mg of paraformaldehyde, 200 mg of cuprous chloride, 1.5 ml of acetic acid and 50 ml of dioxane was stirred at reflux under argon for 75 minutes. A 100 ml portion of dichloromethane was added followed by the addition of 50 ml of 10% aqueous sodium bicarbonate. The phases were separated, sodium chloride was added to the aqueous phase and the aqueous phase was reextracted with dichloromethane. The organic solutions were combined, dried, filtered and concentrated. The residue was purified by chromatography (alumina), giving 1.43 g of the desired product as a yellow oil.

Workup

  1. temperatureat reflux under argon for 75 minutes
  2. customThe phases were separated
  3. additionsodium chloride was added to the aqueous phase
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (alumina)

Sources & evidence

ORD record
ord-96134576eb8d4d9cb89f3bbf58523c53
Source dataset
uspto-grants-1990_08
Patent number
US04952600

Reaction notes

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