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

HRID 1020877Notes

Reaction equation

HRID 1020877 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.CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>>[CH3:16][N:17](/[CH:19]=[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])[CH3:18]

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

tert-Butyl 3-oxopyrrolidine-1-carboxylate (40 g, 216 mmol) was treated with N,N-dimethylformamide dimethyl acetal (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 for 64 h. The resulting brownish-yellow solid obtained as such was collected by filtration, dried and used in the next step without further purification. LC/MS: 241.1 (M+1).

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 for 64 h
  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-e47f7db882fe49cdab390ee819c5dbc3
Source dataset
uspto-grants-2014_05
Patent number
US08716482B2

Reaction notes

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