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

HRID 711310
Notes
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Reaction equation

HRID 711310 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]>C1COCC1>[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
67.5 °C

Procedure

A solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (53.4 kg, 288 mol) in THF (133 kg) was treated with DMF-DMA (103 kg, 864 mol) in THF (472 kg) and heated at 65-70° C. under nitrogen for 20 h. The solution was cooled, evaporated under reduced pressure and solvent switched under distillation to cyclohexane. The resulting slurry was then filtered, cake washed with cyclohexane, and then water. The solids were then dried under vacuum at 35-40° C. to give tert-butyl (3Z)-3-[(dimethylamino)methylene]-4-oxopyrrolidine-1-carboxylate.

Workup

  1. temperatureThe solution was cooled
  2. customevaporated under reduced pressure and solvent
  3. distillationswitched under distillation to cyclohexane
  4. filtrationThe resulting slurry was then filtered
  5. washcake washed with cyclohexane
  6. customThe solids were then dried under vacuum at 35-40° C.

Sources & evidence

ORD record
ord-6b8478964e8f4d1cae774154f0fbf95b
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181262B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes