Dimethylformamide dimethyl acetal → (Z)-tert-butyl 3-((dimethylamino)methylene)-4-oxopyrrolidine-1-carboxylate

HRID 532529Notes

Reaction equation

HRID 532529 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[CH3:14][N:15]([CH:17](OC)OC)[CH3:16]>>[CH3:14][N:15](/[CH:17]=[C:6]1/[CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3][C:2]/1=[O:1])[CH3:16]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylate

Product 1

HCID 56971730(Z)-tert-butyl 3-((dimethylamino)methylene)-4-oxopyrrolidine-1-carboxylate

Conditions

Temperature
105 °C

Procedure

A solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (40 g, 216 mmol) was treated with DMF-DMA (267 g, 2241 mmol) and heated at 105° C. for 40 min. The solution was cooled and evaporated under reduced pressure and the resulting orange solid was treated with hexane (200 mL) and cooled in the refrigerator over the weekend. The resulting brownish-yellow solid obtained as such was collected by filtration, dried and used in the next step without further purification.

Workup

  1. temperatureThe solution was cooled
  2. customevaporated under reduced pressure
  3. additionthe resulting orange solid was treated with hexane (200 mL)
  4. temperaturecooled in the refrigerator over the weekend
  5. customThe resulting brownish-yellow solid obtained
  6. filtrationas such was collected by filtration
  7. customdried
  8. customused in the next step without further purification

Sources & evidence

ORD record
ord-00492b1e93bb400ea9060e37841861ea
Source dataset
uspto-grants-2014_10
Patent number
US08853212B2

Reaction notes

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