Dimethylformamide → benzyl (S)-1-ethylpyrrolidine-3-carboxylate

HRID 928053Notes

Reaction equation

HRID 928053 reaction equation
[CH2:1](Br)[CH3:2].FC(F)(F)C(O)=O.[NH:11]1[CH2:15][CH2:14][C@H:13]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:12]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:1]([N:11]1[CH2:15][CH2:14][C@H:13]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:12]1)[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6332Ethyl Bromide3×HCID 11430Potassium CarbonateHCID 86713356(S)-Benzyl pyrrolidine-3-carboxylate trifluoroacetic acid salt2×

Product 1

HCID 71006998benzyl (S)-1-ethylpyrrolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl bromide (0.21 mL) was added to a mixture of benzyl (S)-pyrrolidine-3-carboxylate trifluoroacetic acid salt (Intermediate 191, 0.897 g), potassium carbonate (0.971 g) and DMF (10 mL) at room temperature and the mixture was stirred for 25 hours. Further ethyl bromide (0.11 mL) was added and stirring was continued for 24 hours. Further ethyl bromide (0.05 mL) was added and stirring was continued for 22 hours. The resultant mixture was diluted with water and extracted with diethyl ether, washed with brine, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo to give benzyl (S)-1-ethylpyrrolidine-3-carboxylate (0.563 g).

Workup

  1. stirringstirring
  2. waitwas continued for 24 hours
  3. stirringstirring
  4. waitwas continued for 22 hours
  5. extractionextracted with diethyl ether
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3ddb63a8d0a4455cbeec8d21f1bd43dc
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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