Dimethylformamide dimethyl acetal → tert-Butyl 3-[(dimethylamino)methylidene]-4-oxopyrrolidine-1-carboxylate

HRID 241548Notes

Reaction equation

HRID 241548 reaction equation
[O:1]([C:6]([N:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]1)=[O:7])[C:2]([CH3:5])([CH3:4])[CH3:3].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>>[CH3:16][N:17]([CH:19]=[C:11]1[C:10](=[O:13])[CH2:9][N:8]([C:6]([O:1][C:2]([CH3:5])([CH3:3])[CH3:4])=[O:7])[CH2:12]1)[CH3:18]

Participants

3

Reactant 2

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

Product 1

HCID 53415260tert-Butyl 3-[(dimethylamino)methylidene]-4-oxopyrrolidine-1-carboxylate

Procedure

A solution of 1-(tert-butoxylcarbonyl)-3-pyrrolidone (4.10 g) and N,N-dimethylformamide dimethyl acetal (30.0 mL) was heated to 140° C. for 1 h. The resulting mixture was cooled to room temperature and concentrated under reduced pressure. The residue was redissolved in a minimum amount of dichloromethane and triturated with hexane to yield a yellow precipitate. LC-MS=241.1 (M+1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was redissolved in a minimum amount of dichloromethane
  3. customtriturated with hexane
  4. customto yield a yellow precipitate

Sources & evidence

ORD record
ord-4febb7ba25a44d73a2ff288fa50b85b8
Source dataset
uspto-grants-2014_02
Patent number
US08653059B2

Reaction notes

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