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

HRID 2280200Notes

Reaction equation

HRID 2280200 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 a refrigerator for 3 days. 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 a refrigerator for 3 days
  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-51c723bd1578473fbb21cd1b0736c8cd
Source dataset
uspto-grants-2015_09
Patent number
US09138426B2

Reaction notes

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