Dimethylformamide dimethyl acetal → Tert-butyl 3-(3-(dimethylamino)acryloyl)pyrrolidine-1-carboxylate

HRID 1530628Notes

Reaction equation

HRID 1530628 reaction equation
[C:1]([CH:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5]1)(=[O:3])[CH3:2].[CH3:16][N:17]([CH:19](OC)OC)[CH3:18]>CN(C=O)C>[CH3:16][N:17]([CH3:19])/[CH:18]=[CH:2]/[C:1]([CH:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5]1)=[O:3]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 25257021tert-Butyl 3-acetylpyrrolidine-1-carboxylate

Product 1

HCID 58408433Tert-butyl 3-(3-(dimethylamino)acryloyl)pyrrolidine-1-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of tert-butyl 3-acetylpyrrolidine-1-carboxylate (3.6 g, 16 mmol), DMF (10 mL), and DMF-DMA (20 mL) was stirred at 140° C. for 16 h. The resultant mixture was extracted with ethyl acetate, washed with brine, dried over MgSO4, filtered, and evaporated to afford tert-butyl 3-((E)-3-(dimethylamino)acryloyl)pyrro-lidine-1-carboxylate (4.44 g, 97% yield) as brown oil. LCMS (ESI) m/z: 213.3 [M-56+H+].

Workup

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-20eaf678dd8b40a4b9b3a270b300e364
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

Loading…